Phenethylamine → Pyrimidine, 5-amino-6-chloro-4-(phenethylamino)-

HRID 1594603Notes

Reaction equation

HRID 1594603 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.CCN(CC)CC.[CH2:17]([NH2:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)CCC>[Cl:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:25][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 97104Pyrimidine, 5-amino-6-chloro-4-(phenethylamino)-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-amino-4,6-dichloropyrimidine (1 mmol) in nBuOH was treated with Et3N (1.2 mmol) and phenethylamine (1.05 mmol) at 80° C. After 12 h, the cooled reaction mixture was evaporated under vacuum and the residue was chromatographed to give 6-chloro-5-amino-4-(phenethylamino)-pyrimidine as a yellow solid. mp 156-157° C.; TLC: Rf=0.41, 50% EtOAc-hexane.

Workup

  1. customthe cooled reaction mixture
  2. customwas evaporated under vacuum
  3. customthe residue was chromatographed

Sources & evidence

ORD record
ord-7fffb70f4e34439c98dbbd368c7cbdce
Source dataset
uspto-grants-2001_09
Patent number
US06284748B1

Reaction notes

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