Cyclohexanol → Cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate

HRID 1946689ノート

反応式

HRID 1946689 の反応式
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:18])[CH:14]=[C:13](Cl)[N:12]=1>C1COCC1>[Cl:10][C:11]1[N:16]=[C:15]([C:17]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:18])[CH:14]=[C:13]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:12]=1

参加物

5

反応物 3

HCID 7966Cyclohexanol2 回HCID 24758Sodium hydride2 回HCID 59446913Cyclohexyl 2,4-dichloropyrimidine-6-carboxylate2 回

生成物 1

HCID 59446909Cyclohexyl 2-chloro-6-(cyclohexyloxy)pyrimidine-4-carboxylate収率 111.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A cold (0° C.) solution of cyclohexanol (2.35 ml; 22.3 mmol) was treated with sodium hydride (534 mg; 22.3 mmol) in dry THF (25 ml) and stirred for 30 min at 0° C. It was slowly added to a cooled (0° C.) solution of cyclohexyl 2,6-dichloropyrimidine-4-carboxylate (Intermediate 31, 3.50 g; 12.72 mmol) in dry THF (70 ml) and the resulting mixture was stirred at 50° C. After 4 h the reaction was treated again with a solution cyclohexanol (0.34 ml; 3.18 mmol) and sodium hydride (76.3 mg; 3.18 mmol) in dry THF (3 mL) obtained as described above and it was stirred for an additional hour. The reaction mixture was concentrated under vacuum and the residue was taken up in EtOAc and the organic layer was washed with water, then brine, dried over MgSO4, filtered off and concentrated under vacuum to afford the title compound (4.80 g, 99%) without further purification.

後処理

  1. additionIt was slowly added to
  2. stirringthe resulting mixture was stirred at 50° C
  3. customobtained
  4. stirringwas stirred for an additional hour
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. washthe organic layer was washed with water
  7. dry with materialbrine, dried over MgSO4
  8. filtrationfiltered off
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-24fbd9be81874c4fb690337f7e9af4ea
出典データセット
uspto-grants-2013_03
特許番号
US08399448B2

反応ノート

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