3-Pentanamine → 6-Chloro-2-methyl-5-nitro-N-(pentan-3-yl)pyrimidin-4-amine

HRID 1245763Notes

Reaction equation

HRID 1245763 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([Cl:12])[N:3]=1.[CH2:13]([CH:15]([NH2:18])[CH2:16][CH3:17])[CH3:14]>C1COCC1>[Cl:12][C:4]1[N:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:18][CH:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidine

Product 1

HCID 159085846-Chloro-2-methyl-5-nitro-N-(pentan-3-yl)pyrimidin-4-amineYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 2-methyl-5-nitro-4,6-dichloro-pyrimidine (208 mg, 1.00 mmol) and 1-ethyl-propyl-amine (87 mg, 1.03 mmol) in 2 ml of dry THF was stirred at −78° C. for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give a green oil. The oil was purified through silica gel column chromatography using chloroform to 1:1 hexane/chloroform as eluent to give the title compound (93 mg, 35%). 1H NMR (CDCl3) δ 7.50 (brs, 1H), 4.29 (m, 1H), 2.51 (s, 3H), 1.4–1.8 (m, 4H), 0.92 (t, 6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give a green oil
  7. customThe oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-c4a27440903a4bcaaa60e26bdfc72ab8
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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