4,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde → HCID 19759043, compound

HRID 1586693Notes

Reaction equation

HRID 1586693 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][N:4]([CH3:8])[C:3]1=[O:9].[CH3:10][C:11]([C:14]1[C:19]([OH:20])=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:17]=[C:16]([CH:25]=[O:26])[N:15]=1)([CH3:13])[CH3:12]>C1(C)C=CC=CC=1.ClCCl.[Zn]>[CH3:13][C:11]([C:14]1[C:19]([OH:20])=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:17]=[C:16]([CH:25]([OH:26])[CH:2]2[CH2:7][CH2:6][O:5][N:4]([CH3:8])[C:3]2=[O:9])[N:15]=1)([CH3:10])[CH3:12]

Participants

6

Reactant 2

HCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehydeHCID 19759044HCID 19759044, compound

Product 1

HCID 19759043HCID 19759043, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.1 g (5.7 mmol) of 4-bromo tetrahydro-2-methyl 2H 1,2-oxazin-3-one, Example 1, 1.2 g (5.1 mmol) of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinecarboxaldehyde, Example 6, and 0.75 g (11 mmol) of zinc dust in 30 mL of toluene was stirred at reflux for 18 hours. The cooled reaction mixture was diluted with dichloromethane and vigorously stirred. The zinc was filtered and washed with dichloromethane. The combined filtrates were evaporated to a foam. The residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane elution) to give 0.70 g (39%) of the title compound as an oil mixture of diastereomers; MS m/e 352 (M+ 1).

Workup

  1. temperatureat reflux for 18 hours
  2. customThe cooled reaction mixture
  3. stirringvigorously stirred
  4. filtrationThe zinc was filtered
  5. washwashed with dichloromethane
  6. customThe combined filtrates were evaporated to a foam
  7. customThe residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane elution)
  8. customto give

Sources & evidence

ORD record
ord-f200e733db104274b93150b285d232b7
Source dataset
uspto-grants-1993_06
Patent number
US05215986

Reaction notes

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