4-Hydroxymethylpyridine → HCID 19787879, compound

HRID 1656510Notes

Reaction equation

HRID 1656510 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:4][CH:3]=1.Cl[C:37](Cl)([O:39][C:40](=[O:46])OC(Cl)(Cl)Cl)Cl.[N:48]1[CH:53]=[CH:52][C:51](CO)=[CH:50][CH:49]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(N(CC)CC)C>[O:8]=[C:7]1[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:27]([CH3:29])[CH3:28])[CH:14]([O:19][Si:20]([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:21])[CH3:22])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:4][CH:3]=[C:2]1[NH:1][C:40]([O:39][CH2:37][C:51]1[CH:52]=[CH:53][N:48]=[CH:49][CH:50]=1)=[O:46]

Participants

7

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 19787914HCID 19787914, compound

Product 1

HCID 19787879HCID 19787879, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (1.1 g) and triphosgene (0.93 g) in dichloromethane at 0° C. was added triethylamine (2.0 mL) and the resulting solution was allowed to stir for 0.5 h. To this solution was added 4-pyridylcarbinol and the resulting solution allowed to stir overnight. The solution was poured into saturated aqueous sodium bicarbonate solution and the product was extracted into dichloromethane. The organic solution was washed (saturated aqueous sodium bicarbonate, water), dried, and evaporated. The resulting oil was purified by chromatography, with methanol:dichloromethane (5:95) as the eluent, to provide 2-[6-oxo-2-phenyl-5-(4-pyridylmethoxycarbonylamino)-1,6-dihydro-1-pyrimidinyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a white solid (0.9 g); TLC: Rf =0.4, methanol:dichloromethane (5:95).

Workup

  1. stirringto stir overnight
  2. extractionthe product was extracted into dichloromethane
  3. washThe organic solution was washed (saturated aqueous sodium bicarbonate, water)
  4. customdried
  5. customevaporated
  6. customThe resulting oil was purified by chromatography, with methanol:dichloromethane (5:95) as the eluent

Sources & evidence

ORD record
ord-75d14d6d6c7144da94efdacd8b12f165
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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