HCID 58169124, compound → HCID 58169510, compound

HRID 1484957Notes

Reaction equation

[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.[Br:10][C:11]1[N:16]=[C:15](Br)[C:14]([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[C:13]([CH3:24])[N:12]=1>C(O)C>[Br:10][C:11]1[N:16]=[C:15]([NH:9][C:7]2[CH:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:5][N:6]=2)[C:14]([C:18]#[C:19][Si:20]([CH3:21])([CH3:23])[CH3:22])=[C:13]([CH3:24])[N:12]=1

Participants

Conditions

Temperature: 21.5 °C

Procedure

At 20° C. (using an ice bath for the temperature control), 3-cyclopropyl-1H-pyrazol-5-amine (1.192 g, 9.68 mmol, 1.5 eq) in ethanol (15 ml) was added into a solution of compound 2,4-dibromo-6-methyl-5-((trimethylsilyl)ethynyl)pyrimidine (2.246 g, 6.45 mmol, 1.0 equiv.) in ethanol (15 mL). The reaction was stirred at for 20 h at 20-23° C. Ethanol was removed under reduced pressure 10-20° C. Purified by silica-gel column chromatography (mobile phase: petroleum ether/ethyl acetate=20/1; 5/1) afforded solid product 2-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-6-methyl-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine (500 mg, 22%). LC-MS (m/z)=392.0 [M+2H]+.

Workup

customAt 20° C.
customEthanol was removed under reduced pressure 10-20° C
customPurified by silica-gel column chromatography (mobile phase: petroleum ether/ethyl acetate=20/1; 5/1)

Sources & evidence

ORD record: ord-89301c48f7f74c3cb64772fe88c4b12d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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