Hydrochloric Acid → HCID 15147492, compound

HRID 255711Notes

Reaction equation

HRID 255711 reaction equation
C(OC([NH:8][C:9]1[C:10]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[N:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][C:14]=1[CH3:15])=O)(C)(C)C.C(O)(C)C.Cl.C(OCC)(=O)C>C(O)C.O>[NH2:8][C:9]1[C:10]([C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)=[N:11][C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:13][C:14]=1[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 15147488HCID 15147488, compound

Product 1

HCID 15147492HCID 15147492, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-tert-butyloxycarbonylamino-6-methyl-2-phenyl-4-(4-pyridyl)pyrimidine (1.5 g) and an isopropanol solution of hydrogen chloride (4 ml, HCl 5 mMol/ml) in ethanol (15 ml) was stirred for 1 hour at 40° C. After cooling to room temperature, the reaction mixture was poured into a suspension of ethyl acetate (100 ml) and water (50 ml) under stirring, and the mixture was adjusted to pH 9.0. The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residual crystal was recrystallized from ether to give 5-amino-6-methyl-2-phenyl-4-(4-pyridyl)pyrimidine, mp 208°-209° C.

Workup

  1. washThe separated organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residual crystal was recrystallized from ether

Sources & evidence

ORD record
ord-7ee07a3da02a4973b97531e0c6f2cfd9
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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