Water → ethyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

HRID 1085702

Reaction equation

HRID 1085702 reaction equation
C([SnH](CCCC)CCCC)CCC.Cl[C:15]([C:25]1[CH:26]=[N:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:29][CH:30]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].N(C(C)(C)C#N)=NC(C)(C)C#N.O>C1(C)C=CC=CC=1>[CH3:34][C:31]([C:28]1[N:27]=[CH:26][C:25]([CH:15]([C:21]([CH3:22])([CH3:24])[CH3:23])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:30][N:29]=1)([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 14718731ethyl (RS)-2-chloro-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

Product 1

HCID 14718703ethyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tri-n-Butyl tin hydride (1.3 cm3) was added to a solution of ethyl (RS)-2-chloro-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate (1.4 g) and a catalytic amount of 2,2'-azobisisobutyronitrile in dry toluene (10 cm3). The mixture was heated to the reflux temperature for a period of 11/2 hours, after which it was cooled to the ambient temperature, poured into water, and extracted into ethyl acetate. After concentration by evaporation of the solvent under reduced pressure, the residue was subjected to column chromatography on silica gel using hexane followed by ethyl acetate as eluent to give ethyl (RS)-2-[2-(1,1-dimethyl-ethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate (1.1 g) as a pale yellow liquid, the spectral data of which were identical to those obtained for the sample generated in Example 9.

Workup

  1. extractionextracted into ethyl acetate
  2. concentrationAfter concentration
  3. customby evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-59209b8456254df4947a588a90c2d9dd
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Linked notes

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