2,4-Dichloro-6-methylpyrimidine → 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-6-methylpyrimidin-4-amine

HRID 1510402Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH:10]1([C:13]2[NH:17][N:16]=[C:15]([NH2:18])[CH:14]=2)[CH2:12][CH2:11]1.C(N(C(C)C)CC)(C)C>C(O)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:18][C:15]2[CH:14]=[C:13]([CH:10]3[CH2:12][CH2:11]3)[NH:17][N:16]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2,4-dichloro-6-methylpyrimidine (30.0 g, 184 mmol), 5-cyclopropyl-1H-pyrazol-3-ylamine (22.6 g, 184 mmol) and diisopropylethylamine (46 mL, 278 mmol) in 1-butanol (50 mL) was heated to 60° C. for 65 h. The reaction was cooled to room temperature and diluted with ethyl acetate. The mixture was washed with 2 N sodium hydroxide, water and brine, then dried over sodium sulfate and concentrated on a rotary evaporator. The residue was treated with a small amount of acetonitrile, sonicated and then triturated with ether until a solid was formed. The solid was collected by filtration to give the desired product (23.0 g, 50%) as a yellow solid.

Workup

temperatureThe reaction was cooled to room temperature
washThe mixture was washed with 2 N sodium hydroxide, water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated on a rotary evaporator
additionThe residue was treated with a small amount of acetonitrile
customsonicated
customtriturated with ether until a solid
customwas formed
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-db4eb6923d5b4cf1922af7cfaec1b2a3
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211929B2

Reaction notes

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