Phosgene → HCID 54171827, compound

HRID 1858275Notes

Reaction equation

HRID 1858275 reaction equation
[Br:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][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][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:16]=2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1.C(N(CC)CC)C.[C:51](Cl)(Cl)=[O:52].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][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][O:22][Si:23]([C:36]([CH3:37])([CH3:38])[CH3:39])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:16]=2)[C:51]1=[O:52]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22125069HCID 22125069, compound

Product 1

HCID 54171827HCID 54171827, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.5 g (6.8 mmol) 5-((2-bromoanilino)methyl)-4-[3-(tert-butyldiphenylsilyloxymethyl)anilino]-2-methylthiopyrimidine and 1.9 ml (13.6 mmol) of triethylamine in 50 ml of toluene was added dropwise to a solution of 7 ml of a 20% solution of phosgene in toluene (13.6 mmol) in a further 50 ml of toluene. The mixture was heated at reflux for 5 hours and the cooled. 50 ml of ethyl acetate and 60 ml of saturated aqueous sodium bicarbonate were added and the mixture separated. The organic phase was dried over magnesium sulfate, filtered and evaporated to afford 4.7 g (100%) of 3-(2-bromophenyl)-1-[3-(tert-butyldiphenylsilyloxymethyl)phenyl]-3,4-dihydro-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a colorless oil. [Mass spectrum (ESI) MH+ =696].

Workup

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

Sources & evidence

ORD record
ord-f79461ffbfb0454394a0478988dc5a34
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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