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

HRID 216167

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]=1

Participants

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 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)].

Workup

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

Sources & evidence

ORD record: ord-b69bbf448dd24273885129db9139e27a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193183B2

Linked notes

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