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

HRID 1280591Notes

Reaction equation

HRID 1280591 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]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:12][C:13]([S:16][CH3:17])=[N:14][CH:15]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].O>O1CCCC1.C(OCC)(=O)C>[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][CH3:17])=[N:14][CH:15]=2)[N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:32]1=[O:33]

Participants

7

Reactant 4

HCID 962WaterHCID 6371Phosgene2×HCID 8471TriethylamineHCID 184254255-(2-Chlorophenyl)aminomethyl-4-phenylamino-2-methylthiopyrimidine

Product 1

HCID 184254393-(2-chlorophenyl)-7-methylthio-1-phenyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A cooled solution of 5-(2-chlorophenyl)aminomethyl-4-phenylamino-2-methylthiopyrimidine (6 g) and 5.2 mL of triethylamine in 75 mL of tetrahydrofuran was added dropwise 8.5 mL of phosgene (20% in toluene) in 35 mL of tetrahydrofuran. The mixture was stirred at room temperature overnight. Additional 3 mL phosgene (20% in toluene) was added to the mixture. After stirring for 15 minutes the mixture was treated with water and ethyl acetate. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography using 10:45 ethyl acetate/hexanes as eluant to give 2.1 g of 3-(2-chlorophenyl)-7-methylthio-1-phenyl-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one as a white solid, m.p. 79.5-82.4° C.

Workup

  1. stirringAfter stirring for 15 minutes the mixture
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-75e0b43ac17d4196bbe76b760d184a06
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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