Phosgene → HCID 22125090, compound

HRID 1858262Notes

Reaction equation

HRID 1858262 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([NH:27][C:28]2[C:33]([CH2:34][NH:35][C:36]3[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:43])=[CH:32][N:31]=[C:30]([S:44][CH3:45])[N:29]=2)[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:53](Cl)(Cl)=[O:54]>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([N:27]2[C:28]3=[N:29][C:30]([S:44][CH3:45])=[N:31][CH:32]=[C:33]3[CH2:34][N:35]([C:36]3[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:43])[C:53]2=[O:54])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 22125119HCID 22125119, compound

Product 1

HCID 22125090HCID 22125090, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.3 g (5 mmol) of 4-[3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenyl]amino-5-(2-chloro-6-methylanilino)methyl-2-methylthiopyrimidine in 50 ml of tetrahydrofuran was treated with 1.4 ml (10 mmol) of triethylamine and the resulting mixture was added dropwise to a solution of 5 ml (9.6 mmol) of phosgene (20% in toluene) in 30 ml of tetrahydrofuran. The mixture was stirred at room temperature for 24 hours and then heated at reflux for a further 18 hours. The mixture was cooled and evaporated. The mixture was partitioned between 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 1.58 g (47%) of 1-[3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenyl]-3-(2-chloro-6-methylphenyl)-3,4-dihydro-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow solid. [Mass spectrum (ESI) MH+ =679].

Workup

  1. temperatureheated
  2. temperatureat reflux for a further 18 hours
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. customThe mixture was partitioned between 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4bd26f3b812f4e70908a4a13cea29087
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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