Water → (2-Isopropylsulfanyl-pyrimidin-4-yl)-methanol

HRID 62869

Reaction equation

HRID 62869 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([S:12][CH:13]([CH3:15])[CH3:14])[N:7]=1)=O)C.[BH4-].[Na+].O>CO>[CH:13]([S:12][C:8]1[N:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][N:9]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 901183312-Isopropylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 90118246(2-Isopropylsulfanyl-pyrimidin-4-yl)-methanolYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 2-isopropylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester (0.1 g, 0.44 mmol) obtained in Step B was dissolved in MeOH (4 mL), NaBH4(0.033 g, 0.9 mmol) was added to the solution, and the mixture was stirred at room temperature for 2 hours. After the termination of the reaction, the reactant was added with water, and then extracted with EtOAc. The separated organic layer was dried with MgSO4 and separated by column chromatography to obtain the title compound (0.063 g, 77%).

Workup

  1. customAfter the termination of the reaction
  2. extractionextracted with EtOAc
  3. dry with materialThe separated organic layer was dried with MgSO4
  4. customseparated by column chromatography

Sources & evidence

ORD record
ord-b31d92927b9e4c29b9f49751a7272251
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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