diff --git a/FreeSql.Tests/FreeSql.Tests/ClickHouse/ClickHouseTest2.cs b/FreeSql.Tests/FreeSql.Tests/ClickHouse/ClickHouseTest2.cs
index 5b21741d..9bc76f41 100644
--- a/FreeSql.Tests/FreeSql.Tests/ClickHouse/ClickHouseTest2.cs
+++ b/FreeSql.Tests/FreeSql.Tests/ClickHouse/ClickHouseTest2.cs
@@ -23,5 +23,126 @@ namespace FreeSql.Tests.ClickHouse
         {
             fsql.CodeFirst.SyncStructure(typeof(CollectDataEntityUpdate01));
         }
+
+        [Fact]
+        public void Issuse1587Test()
+        {
+            fsql.CodeFirst.SyncStructure(typeof(PositionInfoModel));
+        }
+        [Fact]
+        public void Issuse1587TestOnePrimary()
+        {
+            fsql.CodeFirst.SyncStructure(typeof(PositionInfoModel2));
+        }
+    }
+
+    [Table(Name = "table_1")]
+    [Index("stcd_index", "STCD", false)]
+    [Index("tm_index", "TM", false)]
+    [Index("type_index", "TYPE", false)]
+    public class PositionInfoModel
+    {
+        [Column(IsPrimary = true)]
+        public string STCD
+        {
+            set; get;
+        }
+
+        [Column(IsPrimary = true)]
+        public DateTime TM
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public decimal LON
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public decimal LAT
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public int TYPE
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public decimal SPD
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public decimal COG
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public DateTime? UT
+        {
+            set; get;
+        }
+    }
+
+
+    [Table(Name = "table_2")]
+    [Index("stcd_index", "STCD", false)]
+    [Index("tm_index", "TM", false)]
+    [Index("type_index", "TYPE", false)]
+    public class PositionInfoModel2
+    {
+        public string STCD
+        {
+            set; get;
+        }
+
+        [Column(IsPrimary = true)]
+        public DateTime TM
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public decimal LON
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public decimal LAT
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = false)]
+        public int TYPE
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public decimal SPD
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public decimal COG
+        {
+            set; get;
+        }
+
+        [Column(IsNullable = true)]
+        public DateTime? UT
+        {
+            set; get;
+        }
     }
 }
\ No newline at end of file
diff --git a/Providers/FreeSql.Provider.ClickHouse/ClickHouseCodeFirst.cs b/Providers/FreeSql.Provider.ClickHouse/ClickHouseCodeFirst.cs
index b71c024d..d0c41132 100644
--- a/Providers/FreeSql.Provider.ClickHouse/ClickHouseCodeFirst.cs
+++ b/Providers/FreeSql.Provider.ClickHouse/ClickHouseCodeFirst.cs
@@ -199,7 +199,7 @@ namespace FreeSql.ClickHouse
                                 sb.Remove(sb.Length - 2, 2);
                                 sb.Append(" )");
                                 sb.Append(" \r\nPRIMARY KEY ");
-                                sb.Append(ls);
+                                sb.Append($"({ls})   ");
                                 sb.Remove(sb.Length - 2, 2).Append(",");
                             }
 
@@ -415,7 +415,7 @@ where a.database in ({0}) and a.table in ({1})", tboldname ?? tbname);
                         sb.Remove(sb.Length - 2, 2);
                         sb.Append(" )");
                         sb.Append(" \r\nPRIMARY KEY ");
-                        sb.Append(ls);
+                        sb.Append($"({ls})   ");
                         sb.Remove(sb.Length - 2, 2).Append(",");
                     }
 
@@ -455,7 +455,8 @@ where a.database in ({0}) and a.table in ({1})", tboldname ?? tbname);
                         .Append(_commonUtils.QuoteSqlName(tbname[0], tbname[1])).Append(";\r\n");
                 }
 
-                return sb.Length == 0 ? null : sb.ToString();
+                var res = sb.Length == 0 ? null : sb.ToString();
+                return res;
             }
             finally
             {
@@ -514,9 +515,14 @@ where a.database in ({0}) and a.table in ({1})", tboldname ?? tbname);
             }
             string CkNullableAdapter(string dbType, bool isPrimary)
             {
-                return isPrimary
-                    ? dbType.Replace("Nullable(", "").Replace(")","").Replace(" NOT NULL", "")
-                    : dbType.Replace(" NOT NULL", "");
+                return isPrimary switch
+                {
+                    true when dbType.Contains("Nullable") => dbType.Replace("Nullable(", "")
+                        .Replace(")", "")
+                        .Replace(" NOT NULL", ""),
+                    true => dbType,
+                    _ => dbType.Replace(" NOT NULL", "")
+                };
             }