Diisopropylethylamine → 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-pyrimidin-4-amine

HRID 450366Notes

Reaction equation

HRID 450366 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH:12]1([C:15]2[NH:19][N:18]=[C:17]([NH2:20])[CH:16]=2)[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:20][C:17]2[CH:16]=[C:15]([CH:12]3[CH2:14][CH2:13]3)[NH:19][N:18]=2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 866217662-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-pyrimidin-4-amineYield 72.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dichloro-5-nitropyrimidine (2 g) and 5-cyclopropyl-1H-pyrazol-3-amine (2 g) in acetonitrile (20 mL) with diisopropylethylamine (2 mL) was stirred at room temperature for 24 hours, The resulting mixture was concentrated, and the resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to afford 2.1 g desired product. MS (electrospray): 281 (M+1) for C10H9ClN6O2.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

Sources & evidence

ORD record
ord-fd4b18d3f55644bba02f743b2b4ca2ae
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

Loading…