Water → 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 379601Notes

Reaction equation

HRID 379601 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][C:14]1[S:29][C:17]2[N:18]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:16]=2[C:15]=1[S:30][CH:31]([CH3:33])[CH3:32].O>CN(C)C=O>[N:1]1([CH2:13][C:14]2[S:29][C:17]3[N:18]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:19](=[O:24])[N:20]([CH3:23])[C:21](=[O:22])[C:16]=3[C:15]=2[S:30][CH:31]([CH3:33])[CH3:32])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 183666156-(chloromethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

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)-dioneYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzimidazole (0.083 g) and sodium hydride (60% dispersion, 0.031 g) were added to 6-(chloromethyl)-3-methyl-5-[(1-methylethyl)thio]-1-(2-methylpropyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.21 g) in dry dimethylformamide (10 ml) and the reaction was stirred for 2 hours at room temperature. Water was added to the reaction mixture which was then extracted with ethyl acetate (3×50 ml). The combined organic phases were washed with brine and dried, filtered and evaporated. The residue was triturated with diethyl ether to give the title compound (0.163 g).

Workup

  1. extractionwas then extracted with ethyl acetate (3×50 ml)
  2. washThe combined organic phases were washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-82e0af729210440ebc98861ff77d6cb3
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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