Phosgene → HCID 22125024, compound

HRID 1858241Notes

Reaction equation

HRID 1858241 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:3]=1[NH:4][CH2:5][C:6]1[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]CO)[CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.C(N(CC)CC)C.[C:36]([Cl:39])(Cl)=O.[O:40]1CCC[CH2:41]1>>[Cl:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([Cl:1])[C:3]=1[N:4]1[CH2:5][C:6]2[C:7](=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=2)[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:36][Cl:39])[CH:16]=2)[C:41]1=[O:40]

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 22125011HCID 22125011, compound

Product 1

HCID 22125024HCID 22125024, compoundYield 50%

Procedure

A solution of 1 g (2.3 mmol) of 5-(2,6-dichloroanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine in 60 ml of tetrahydrofuran was treated with 0.8 ml (6 mmol) of triethylamine and the mixture was added dropwise to a solution of 1.8 ml of phosgene (20% in toluene) in 40 ml of tetrahydrofuran. The cooling was removed. After 2 hours 100 ml of saturated aqueous ammonium chloride solution were added. The mixture was separated and the organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel using diethyl ether/hexane (1:2) for the elution. Product-containing fractions were combined and evaporated to give 0.5 g (50%) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydro-1-[3-(2-chloroethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =479].

Workup

  1. customThe cooling was removed
  2. additionAfter 2 hours 100 ml of saturated aqueous ammonium chloride solution were added
  3. customThe mixture was separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. washfor the elution
  8. customevaporated

Sources & evidence

ORD record
ord-7aac701781d747a7aa751ebd511d50f8
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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