Butylamine → 6-Chloro-5-amino-4-butyl pyrimidine

HRID 1295465

Reaction equation

HRID 1295465 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].CCN(CC)CC.[CH2:17](N)[CH2:18][CH2:19][CH3:20]>CCCCO>[Cl:8][C:7]1[N:6]=[CH:5][N:4]=[C:3]([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 858276526-Chloro-5-amino-4-butyl pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-amino-4,6-dichloropyrimidine (1 mmol) in n-BuOH was treated with Et3N (1.2 mmol) and n-Butylamine (1.0 mmol) at 80 C. After 16 h, solvent was removed under reduced pressure. The residue was dissolved in EtOAc, the organic layer washed with water and then dried (MgSO4). Filtration and removal of solvent gave 6-chloro-5-amino-4-butyl pyrimidine as a brown solid. Rf=0.5 in 1:1 EtOAc:hexane. 1H NMR (CDCl3) δ 8.07 (s, 1H), 4.88 (br s, 1H), 3.49 (m, 2H), 3.35 (br s, 2H), 1.6 (m, 2H), 1.44 (m, 2), 0.95 (t, 3H).

Workup

  1. customsolvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic layer washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-4c96a5f9caf744acb1e89ce41d429c2c
Source dataset
uspto-grants-2007_07
Patent number
US07241890B2

Linked notes

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