Hydrochloric Acid → 6-(chloromethyl)-3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
Reaction equation
[CH2:1]=[O:2].C[N:4]1[C:9](=O)[C:8]2[CH:11]=[CH:12][S:13][C:7]=2[N:6]([CH:14]([CH3:16])[CH3:15])[C:5]1=[O:17].[C:18](OCC)(=O)C.[ClH:24]>>[Cl:24][CH2:18][C:12]1[S:13][C:7]2[N:6]([CH:14]([CH3:15])[CH3:16])[C:5](=[O:17])[N:4]([CH3:9])[C:1](=[O:2])[C:8]=2[CH:11]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Aqueous formaldehyde (37%, 2.5 ml) was added to a stirred solution of 3-methyl-1-(1-methylethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1.0 g) in concentrated hydrochloric acid (5 ml) at 0° C. The mixture was saturated with hydrogen chloride gas and stirred at 0° C. for 3 hours and then at room temperature for 3 days. Ethyl acetate (100 ml) was added, the mixture was washed with water (100 ml) and then with saturated aqueous sodium bicarbonate solution (100 ml), then dried over anhydrous magnesium sulfate, filtered and evaporated to give the subtitle compound (1.1 g).
Workup
- waitat room temperature for 3 days
- washthe mixture was washed with water (100 ml)
- dry with materialwith saturated aqueous sodium bicarbonate solution (100 ml), then dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c7adc1211dd84281b589b36e5e0f4b92
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300334B1
Reaction notes
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