Diisopropylethylamine → 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-5-nitropyrimidin-4-amine

HRID 1092231Notes

Reaction equation

HRID 1092231 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:16]=[C:15](Cl)[C:14]([N+:18]([O-:20])=[O:19])=[C:13]([CH3:21])[N:12]=1.CCN(C(C)C)C(C)C>CCCCO.CCCCCC>[Cl:10][C:11]1[N:16]=[C:15]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)[C:14]([N+:18]([O-:20])=[O:19])=[C:13]([CH3:21])[N:12]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2752942,4-Dichloro-6-methyl-5-nitropyrimidineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 866217652-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-5-nitropyrimidin-4-amineYield 99.4%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 5-cyclopropyl-1H-pyrazol-3-amine (1.8 g, 14.0 mmol) in n-BuOH (25 ml) was slowly added to the n-BuOH (60 ml) solution of 2,4-dichloro-6-methyl-5-nitropyrimidine (3.0 g, 14.0 mmol) and DIEA (2.4 g, 19.0 mmol). After 5 minutes, the reaction was diluted with hexane (100 ml). The resulting precipitate was collected by filtration to yield the title compound (4.1 g, 96%). MS: Calcd.: 294; Found: [M+H]+ 295.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-fc6bfb2099fd409bac2d0e9f032e6a4c
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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