Methanol → HCID 118024054, compound

HRID 2171790Notes

Reaction equation

HRID 2171790 reaction equation
[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14](/[CH:15]=[CH:16]\[OH:17])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[BH4-].[Na+]>O>[CH:1]1([C:7]2[S:19][C:10]3[N:11]=[C:12]([CH3:18])[N:13]=[C:14]([CH2:15][CH2:16][OH:17])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 136951116HCID 136951116, compound

Product 1

HCID 118024054HCID 118024054, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (Z)-2-(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)ethenol (430 mg) and MeOH (10 mL) was added NaBH4 (65 mg) in small divided portions, followed by stirring for 15 minutes. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed sequentially with a saturated aqueous NH4Cl solution and brine, and dried over Na2SO4, and the residue was purified by silica gel column (hexane/EtOAc) to obtain 2-(6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)ethanol (315 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed sequentially with a saturated aqueous NH4Cl solution and brine
  3. dry with materialdried over Na2SO4
  4. customthe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-bd71cf25f16f4ce1923e3a50ee7536d7
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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