Tetrahydrofuran → {2-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol

HRID 216167

反応式

HRID 216167 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:8]=[C:7]([Cl:22])[N:6]=1)=O.[BH4-].[Li+].C1COCC1>C(COC)OC>[Cl:22][C:7]1[N:6]=[C:5]([CH2:3][OH:2])[CH:10]=[C:9]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N:8]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 576360902-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester2 回

生成物 1

HCID 57636064{2-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol収率 96%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
3 °C

実験手順

A mixture of 2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidine-4-carboxylic acid methyl ester [7.43 g, 23.09 mmol, Intermediate (55)] in dimethoxyethane (100 mL) is chilled in an ice/water bath to 3° C. and treated dropwise via syringe with a solution of 2M lithium borohydride in THF (17.3 mL, 34.6 mmol) not allowing the reaction temperature to exceed 7° C. After complete addition stirring is continued at 5° C. for 1 hour. The reaction mixture is poured into ice/water (250 mL) and extracted four times EtOAc (100 mL). The combined organic extracts are washed with water (100 μL), them with brine (100 mL), dried over magnesium sulfate, filtered and concentrated by rotary evaporator to afford {2-chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol [6.51 g, 96%, Intermediate (57)].

後処理

  1. customto exceed 7° C
  2. additionAfter complete addition
  3. extractionextracted four times EtOAc (100 mL)
  4. washThe combined organic extracts are washed with water (100 μL), them with brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporator

出典と根拠

ORDレコード
ord-b69bbf448dd24273885129db9139e27a
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

関連ノート

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