Tetrahydrofuran → {2-Chloro-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-methanol
Reaction equation
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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 3 °C
Procedure
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 2 M 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 mL), 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)].
Workup
- customto exceed 7° C
- additionAfter complete addition
- extractionextracted four times EtOAc (100 mL)
- washThe combined organic extracts are washed with water (100 mL), them with brine (100 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated by rotary evaporator
Sources & evidence
- ORD record
- ord-c5d6acf64d2341feb8cbead16cab3e26
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07517889B2
Reaction notes
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