Potassium Carbonate → HCID 54423567, compound

HRID 1588485Notes

Reaction equation

HRID 1588485 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([CH3:15])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH:24][CH3:25]>CC(C)=O>[NH:8]([C:6]1[CH:5]=[C:4]([CH3:15])[N:3]=[C:2]([NH:1][CH2:22][CH:23]=[CH:24][CH3:25])[N:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 6082032-Amino-4-phenylamino-6-methylpyrimidine

Product 1

HCID 54423567HCID 54423567, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-amino-4-anilino-6-methylpyrimidine (1 g) (5 mM), potassium carbonate (0.4 g, 5.5 mM), crotyl bromide (0.61 ml) (5 mM) and acetone (25 ml) was heated at reflux for 20 hours. The solvent was then evaporated and the residue triturated with methylene chloride. The methylene chloride extracts were combined and the solvent removed by evaporation. The residual syrup was purified by flash chromatography using Merck 9835 silica (200 g) and eluting with 5% v/v methanol/methylene chloride. There thus was obtained 4-anilino-2-crotylamino-6-methylpyrimidine as a viscous oil (0.36 g) which was used without characterisation.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. customThe solvent was then evaporated
  4. customthe residue triturated with methylene chloride
  5. customthe solvent removed by evaporation
  6. customThe residual syrup was purified by flash chromatography
  7. washeluting with 5% v/v methanol/methylene chloride

Sources & evidence

ORD record
ord-817b25c9f61c43bf9f4ae527910e5c9d
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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