Sodium Carbonate → 4-Pivaloylamino-6-chloro-2-ethylaminopyrimidine

HRID 2120689Notes

Reaction equation

HRID 2120689 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH2:10][CH3:11])[N:3]=1.[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>CCN(CC)CC>[C:12]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH2:10][CH3:11])[N:3]=1)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride2×HCID 234355296-Chloro-N2-ethylpyrimidine-2,4-diamine

Product 1

HCID 234354844-Pivaloylamino-6-chloro-2-ethylaminopyrimidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

A mixture of the pyrimidine 18-2 (3.76 g, 21.8 mmol), pivaloyl chloride (10.7 mL, 87 mmol), Et3N (15.2 mL, 109 mmol) and TEF (80 mL) were stirred at room temperature for 24 hours. A further 3 mL of pivaloyl chloride and 4 mL of Et3N was added and the mixture stirred for another 24 hours. The solution was poured into saturated Na2CO3, extracted with EtOAc (2×), washed with brine, dried (MgSO4) and filtered through a pad of silica gel. Removal of the solvent afforded an orange solid. Trituration with ether/hexane ˜20:1 and filtration provided the title compound 18-4 as a white solid.

Workup

  1. stirringthe mixture stirred for another 24 hours
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a pad of silica gel
  6. customRemoval of the solvent
  7. customafforded an orange solid
  8. filtrationTrituration with ether/hexane ˜20:1 and filtration

Sources & evidence

ORD record
ord-7c800ecb326748f9b6d50397ac3a35a9
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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