Sodium borohydride → 2,2-dimethyl-6-(pyrimidin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

HRID 2364002Notes

Reaction equation

HRID 2364002 reaction equation
[CH3:1][C:2]1([CH3:22])[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=3)[S:10][C:5]=2[C:4](=[O:21])[NH:3]1.[BH4-].[Na+]>C(O)C.CO>[CH3:1][C:2]1([CH3:22])[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][N:12]=3)[S:10][C:5]=2[C:4](=[O:21])[NH:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 667437202,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 667502872,2-dimethyl-6-(pyrimidin-4-yl)-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneYield 46.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-6-[2-(methylsulfonyl)pyrimidin-4-yl]-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (0.034 g, 0.10 mmol) in ethanol (2 mL) and methanol (15 mL) was added sodium borohydride (0.092 g, 2.4 mmol) in four portions over 20 min, and the reaction was stirred at room temperature for 15 h. Then, the reaction mixture was concentrated, the residue was dissolved in water (15 mL), and the solution was extracted with 75:25 ethyl acetate/tetrahydrofuran (2×40 mL). The combined organic layers were washed with brine (30 mL), dried over magnesium sulfate, filtered, and concentrated, and the residue was purified by flash chromatography (silica gel, ethyl acetate to 90:10 ethyl acetate/methanol) to give the title compound (0.012 g, 46%) as a yellow solid:

Workup

  1. concentrationThen, the reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water (15 mL)
  3. extractionthe solution was extracted with 75:25 ethyl acetate/tetrahydrofuran (2×40 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by flash chromatography (silica gel, ethyl acetate to 90:10 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-f90352df4de3429c8fa01650708014fb
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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