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

HRID 1092232Notes

Reaction equation

HRID 1092232 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.CCN(C(C)C)C(C)C.[CH:21]1([C:24]2[NH:28][N:27]=[C:26]([NH2:29])[CH:25]=2)[CH2:23][CH2:22]1>CCCCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:29][C:26]2[CH:25]=[C:24]([CH:21]3[CH2:23][CH2:22]3)[NH:28][N:27]=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 73.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2,4-dichloro-5-nitropyrimidine (3.0 g, 15 mmol) and DIEA (2.4 g, 18.5 mmol) in n-BuOH (30 ml) was slowly added 5-cyclopropyl-1H-pyrazol-3-amine (2.0 g, 16.2 mmol) at 25° C. The resulting solution was stirred at 25° C. for 5 minutes and concentrated to dryness to give the title compound (3.1 g). NMR (CDCl3) 0.80 (m, 2H), 1.05 (m, 2H), 6.60 (s, 1H), 9.20 (s, 1H), 9.70 (br s, 1H), 10.40 (br s, 1H).

Workup

  1. customat 25° C
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-be9c7c485b8b484890a1b5a0da8e0fed
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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