Water → 7-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[C:11]([NH2:24])=[N:12][C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:14][CH:15]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][C:10]2[C:11](=[N:12][C:13]([S:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[NH:24][C:32]1=[O:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution, cooled to −10° C., of 5-(2-chlorophenyl) aminomethyl-4-amino-2-benzylthiopyrimidine (4.3 g, 12.1 mmol) in 100 mL of tetrahydrofuran was added triethylamine (3.1 mL, 22.2 mmol). This solution was then treated dropwise with a solution of phosgene (6.15 mL of 20% solution in toluene; 11.8 mmol). After stirring for 30 minutes, additional triethylamine (1.0 mL, 7.1 mmol) was added followed by phosgene (2.0 mL of 20% solution in toluene; 3.8 mmol). The reaction was warmed to room temperature, treated with 0.5 mL water and stirred for 30 minutes. The reaction was then filtered and the mother liquor was concentrated and stirred with dichloromethane. The product was then collected by vacuum filtration and dried in vacuo to give 3.83 g of 3-(2-chlorophenyl)-7-benzylthio-3,4-dihydropyrimido-[4,5-d]pyrimidin-2(1H)-one as a white solid (sulfide 8.1).
Workup
- stirringstirred for 30 minutes
- filtrationThe reaction was then filtered
- concentrationthe mother liquor was concentrated
- stirringstirred with dichloromethane
- filtrationThe product was then collected by vacuum filtration
- customdried in vacuo
Sources & evidence
- ORD record
- ord-7802dd43eb1a496685527331f6e88cb3
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451804B1
Reaction notes
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