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

HRID 415436Notes

Reaction equation

HRID 415436 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-e315ad1328b74f7bbbfb1e47c1801534
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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