Isopropylamine → 6-Chloro-N4-isopropylpyrimidine-4,5-diamine

HRID 1518330Notes

Reaction equation

HRID 1518330 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[CH3:10][CH:11]([NH2:13])[CH3:12].CCN(CC)CC>>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][CH:11]([CH3:12])[CH3:10])[C:7]=1[NH2:8]

Participants

4

Reactant 3

HCID 6363Isopropylamine2×HCID 8471TriethylamineHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 71471626-Chloro-N4-isopropylpyrimidine-4,5-diamine

Procedure

4,6-Dichloropyrimidin-5-amine (492 mg, 3 mmol), propan-2-amine (284 μl, 3.3 mmol) and Et3N (836 μl, 6 mmol) were combined and heated at reflux. The mixture was refluxed for 5 days and each day additional isopropylamine (0.77 mL, 9 mmol) was added. The reaction mixture was cooled to room temperature, concentrated, slurried in water, filtered, rinsed with additional water and dried under reduced pressure to provide the title compound 52A as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.72 (1H, s), 6.53 (1H, d), 5.02 (2H, s), 4.20 (1H, octet), 1.18 (6H, d).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. additionwas added
  4. concentrationconcentrated
  5. filtrationfiltered
  6. washrinsed with additional water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-e8a70a148bca45d69f05c9526ae0b881
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…