Ethanol → 6-(1H-Benzimidazol-1-ylmethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379599Notes

Reaction equation

HRID 379599 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:16][CH:17]([CH3:19])[CH3:18])=[C:12]([CH:14]=O)[S:13][C:7]=2[N:6]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:5]1=[O:24].[CH2:25](O)[CH3:26]>O>[N:4]1([CH2:14][C:12]2[S:13][C:7]3[N:6]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:5](=[O:24])[N:4]([CH3:3])[C:9](=[O:10])[C:8]=3[C:11]=2[S:16][CH:17]([CH3:19])[CH3:18])[C:9]2[CH:8]=[CH:11][CH:12]=[CH:25][C:26]=2[N:6]=[CH:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 183665731,2,3,4-Tetrahydro-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 183666216-(1H-Benzimidazol-1-ylmethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.11 g) was added to 1,2,3,4-tetrahydro-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-6-carboxaldehyde (0.50 g) in ethanol (20 ml) and the mixture was stirred for 24 hours. The reaction was diluted with water (50 ml) and was then extracted with ethyl acetate (3×50 ml). The organic phases were washed with brine and then dried, filtered and evaporated to give the subtitle compound as a yellow solid (0.45 g).

Workup

  1. extractionwas then extracted with ethyl acetate (3×50 ml)
  2. washThe organic phases were washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0ca9d0697f254f8d833948d11c2c88b1
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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