Phosgene → HCID 18425455, compound

HRID 1858182Notes

Reaction equation

HRID 1858182 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 g (15.2 mmol) of 5-(2,6-dichlorophenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine and 4 ml (29 mmol) of triethylamine 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-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one 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-64a809f5efd341f5a26475245c8dfb19
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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