Phosgene → HCID 67063139, compound

HRID 599271Notes

Reaction equation

HRID 599271 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)=[CH:8][N:7]=[C:6]([S:22][CH3:23])[N:5]=1)[CH3:2].CCN(CC)CC.[C:31](Cl)(Cl)=[O:32]>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:1]([N:3]1[C:4]2=[N:5][C:6]([S:22][CH3:23])=[N:7][CH:8]=[C:9]2[CH2:10][N:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=2)[C:31]1=[O:32])[CH3:2]

Participants

7

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 67063002HCID 67063002, compound

Product 1

HCID 67063139HCID 67063139, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-ethyl-5-((4-fluoro-3-nitrophenylamino)methyl)-2-(methylthio)pyrimidin-4-amine (2.20 g, 6.5 mmol) in CH2Cl2 (25 mL) was added Et3N (2.7 mL, 20 mmol) followed by phosgene (20% solution in toluene, 4.3 mL, 7.8 mmol). The reaction mixture was stirred for 2 h at RT and then diluted with water. The organic layer was separated and washed with brine, dried (MgSO4) and concentrated to provide an orange yellow solid, which on stirring in ethyl acetate followed by filtration provided 1-ethyl-3-(4-fluoro-3-nitrophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a light yellow solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto provide an orange yellow solid, which
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-b05303f5b36a4264abc3016efd5495bd
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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