Sodium Hydroxide → 5-Benzyloxy-1-methyl-6-oxo-2-p-tolylmethanesulfonyl-amino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide

HRID 1409594Notes

Reaction equation

HRID 1409594 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[N:9]([CH3:27])[C:10](=[O:26])[C:11]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]([NH:16][CH3:17])=[O:15])[N:13]=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36](Cl)(=[O:38])=[O:37])=[CH:31][CH:30]=1.[OH-].[Na+]>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH3:17][NH:16][C:14]([C:12]1[NH:13][C:8]([NH2:7])([S:36]([CH2:35][C:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][CH:31]=2)(=[O:38])=[O:37])[N:9]([CH3:27])[C:10](=[O:26])[C:11]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:15]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 2794648(4-Methylphenyl)methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 867102892-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Product 1

HCID 1317322065-Benzyloxy-1-methyl-6-oxo-2-p-tolylmethanesulfonyl-amino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamideYield 46%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (93.8 mg, 836 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 μmol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of (4-methylphenyl)methanesulfonyl chloride (93.7 mg, 458 μmol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2% MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46%). LCMS: m/z=457 (MH+).

Workup

  1. temperaturethe reaction mixture was cooled by an ice bath
  2. waitAfter 70 min.
  3. extractionThe organic phase was extracted with EtOAc
  4. washThe combined organic phases were washed with water, and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1e416b9e25694165ab4ad6799b502a63
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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