Methylhydrazine → 4-(azetidin-1-yl)-3-(5-bromo-1-methyl-1H-pyrazol-4-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 72726Notes

Reaction equation

[CH3:1][NH:2][NH2:3].[N:4]1([C:8]2[C:13]([C:14]([C:16]3[CH:17]=[N:18][N:19]([CH3:22])[C:20]=3[Br:21])=O)=[C:12](Cl)[N:11]=[CH:10][N:9]=2)[CH2:7][CH2:6][CH2:5]1>N1C=CC=CC=1>[N:4]1([C:8]2[N:9]=[CH:10][N:11]=[C:12]3[N:2]([CH3:1])[N:3]=[C:14]([C:16]4[CH:17]=[N:18][N:19]([CH3:22])[C:20]=4[Br:21])[C:13]=23)[CH2:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of methylhydrazine (98%, 1.57 mL, 29.2 mmol) and [4-(azetidin-1-yl)-6-chloropyrimidin-5-yl](5-bromo-1-methyl-1H-pyrazol-4-yl)methanone (C27) (1.04 g, 2.92 mmol) in pyridine (15 mL) was heated to 85° C. for 16 hours. Volatiles were removed in vacuo and the residue was purified using silica gel chromatography (Gradient: 0.5% to 5% methanol in ethyl acetate) to provide the product as a solid. Yield: 960 mg, 2.76 mmol, 94%. LCMS m/z 348.3, 350.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.25-2.34 (m, 2H), 3.84-4.04 (br m, 4H), 3.97 (s, 3H), 4.05 (s, 3H), 7.67 (s, 1H), 8.39 (s, 1H).

Workup

customVolatiles were removed in vacuo
customthe residue was purified

Sources & evidence

ORD record: ord-9a2e571f0b2d4b79a6c5568609fcee17
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829010B2

Reaction notes

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