Water → 7-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 478584Notes

Reaction equation

HRID 478584 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>[CH2:17]([S:16][C:13]1[N:12]=[C:11]2[NH:24][C:32](=[O:33])[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:9][C:10]2=[CH:15][N:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371Phosgene2×HCID 8471Triethylamine2×HCID 180024735-(2-Chlorophenyl) aminomethyl-4-amino-2-benzylthiopyrimidine

Product 1

HCID 129913387-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution, cooled to −10° C., of 4.3 g (12.1 mmol) of 5-(2-chlorophenyl) aminomethyl-4-amino-2-benzylthiopyrimidine in 100 mL of tetrahydrofuran was added 3.1 mL (22.2 mmol) of triethylamine. This solution was then treated dropwise with a solution of 6.15 mL of phosgene (20% solution in toluene; 11.8 mmol) After stirring for 30 minutes, an additional 1.0 mL of triethylamine (7.1 mmol) was added followed by 2.0 mL of phosgene (20% solution in toluene; 3.8 mmol). The reaction was warmed to room temperature, treated with 0.5 mL H2O 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 7-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one as a white solid.

Workup

  1. stirringstirred for 30 minutes
  2. filtrationThe reaction was then filtered
  3. concentrationthe mother liquor was concentrated
  4. stirringstirred with dichloromethane
  5. filtrationThe product was then collected by vacuum filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6bdd4b988dab40e495d9d083c1b01198
Source dataset
uspto-grants-2003_11
Patent number
US06642241B1

Reaction notes

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