Phosgene → (2-[3-[3-(2,6-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

HRID 1858317Notes

Reaction equation

HRID 1858317 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]([CH3:36])([CH3:35])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[C:22]([CH2:23][NH:24][C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])=[CH:21][N:20]=[C:19]([S:33][CH3:34])[N:18]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:45](Cl)(Cl)=[O:46].C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]([CH3:36])([CH3:35])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:17]3=[N:18][C:19]([S:33][CH3:34])=[N:20][CH:21]=[C:22]3[CH2:23][N:24]([C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])[C:45]2=[O:46])[CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 54342542HCID 54342542, compound

Product 1

HCID 54285378(2-[3-[3-(2,6-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

A solution of 320 mg (0.6 mmol) of (2-(3-[5-[(2,6-dichlorophenylamino)-methyl]-2-methylthiopyrimidin-4-yl-amino]-phenyl)-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester in 40 ml of toluene was treated with 0.25 ml (1.8 mmol) of triethylamine and the resulting solution was added dropwise to a solution of phosgene (0.6 ml of a 20% solution in toluene) in a further 40 ml of toluene. The mixture was heated at reflux for 1 hour and then cooled. 80 ml of ethyl acetate and 80 ml of water were added. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 350 mg (100%) of (2-[3-[3-(2,6-dichlorophenyl)-7-methylthio-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-1,1-dimethylethyl)-carbamic acid tert-butyl ester as a white solid. [Mass spectrum (ESI) MH+ =588].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-607431536d13421ca8adffff72754e4e
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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