Water → 6-[(1H-Benzimidazol-1-yl)methyl]-3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379577Notes

Reaction equation

HRID 379577 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18]1[S:32][C:21]2[N:22]([CH:29]([CH3:31])[CH3:30])[C:23](=[O:28])[N:24]([CH3:27])[C:25](=[O:26])[C:20]=2[CH:19]=1.O>CN(C)C=O>[N:1]1([CH2:17][C:18]2[S:32][C:21]3[N:22]([CH:29]([CH3:30])[CH3:31])[C:23](=[O:28])[N:24]([CH3:27])[C:25](=[O:26])[C:20]=3[CH:19]=2)[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 11430Potassium CarbonateHCID 183666266-(chloromethyl)-3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 183666196-[(1H-Benzimidazol-1-yl)methyl]-3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzimidazole (0.395 g) and potassium carbonate (1 g) were added to a stirred solution of 6-(chloromethyl)-3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.55 g) in anhydrous dimethylformamide (5 ml) at room temperature. After 2 days, water (50 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The organic extracts were dried over anhydrous magnesium sulfate and filtered through a silica pad which was washed with ethyl acetate. The filtrate was evaporated and the residue was purified twice by normal-phase preparative HPLC with gradient dichloromethane/ethanol elution to give the title compound (0.394 g) as a foam.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered through a silica pad which
  4. washwas washed with ethyl acetate
  5. customThe filtrate was evaporated
  6. customthe residue was purified twice by normal-phase preparative HPLC with gradient dichloromethane/ethanol elution

Sources & evidence

ORD record
ord-860c5f7c6b3143889ba5de956e569417
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

Loading…