Phosgene → HCID 18425455, compound

HRID 1280553Notes

Reaction equation

HRID 1280553 reaction equation
[C:1]([Cl:4])(Cl)=O.ClC1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[NH:13][CH2:14][C:15]1[C:16]([NH:23][CH3:24])=[N:17][C:18]([S:21][CH3:22])=[N:19][CH:20]=1.C(N(CC)CC)C.[Cl-].[NH4+].[O:34]1CCC[CH2:35]1>>[Cl:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:1]([Cl:4])[C:7]=1[N:13]1[CH2:14][C:15]2[C:16](=[N:17][C:18]([S:21][CH3:22])=[N:19][CH:20]=2)[N:23]([CH3:24])[C:35]1=[O:34]

Participants

6

Reactant 5

HCID 6371PhosgeneHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 18425436HCID 18425436, compound

Product 1

HCID 18425455HCID 18425455, compoundYield 89%

Procedure

A stirred solution, cooled in ice, of 12 mL of phosgene (20% solution in toluene; 23 mmol) in 100 mL of tetrahydrofuran was treated dropwise with a solution of 5-(2,6-dichlorophenyl)aminomethyl-4-methylamino-2-methylthio-pyrimidine (5 g, 15.2 mmol) and triethylamine (4 mL, 29 mmol) in 80 mL of tetrahydrofuran. After stirring for 1 hour the mixture was treated with 100 mL of saturated aqueous ammonium chloride solution and the phases were separated. The aqueous phase was extracted with 100 mL of tetrahydrofuran and the combined organic solutions were dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 4.8 g (89%) of 3-(2,6-dichlorophenyl)-7-methylthio-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (sulfide 1.1) as a white solid.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with 100 mL of tetrahydrofuran
  3. dry with materialthe combined organic solutions were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f555fbcfdab4ba7b4d07955e2d1d091
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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