Thionyl Chloride → 5-(6'-(Chloromethyl)-3-fluorobiphenyl-4-yl)pyrazin-2-amine

HRID 1523860Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:21]O)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.O=S(Cl)[Cl:25]>C(Cl)Cl>[Cl:25][CH2:21][C:16]1[C:15]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[C:13]([F:14])[CH:12]=2)=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of (4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-yl)methanol (1.8 g, 6.1 mmol) and SOCl2 (6 mL) in DCM (20 mL) was stirred at 70° Celsius for 4 hours. The reaction mixture was cooled to rt and concentrated to dryness to give 5-(6′-(chloromethyl)-3-fluorobiphenyl-4-yl)pyrazin-2-amine (1.86 g, 98%). 1H NMR (300 MHz, DMSO-d6) δ 8.40 (s, 1H), 8.04 (s, 1H), 7.96 (m, 1H), 7.66-7.57 (m, 1H), 7.51-7.42 (m, 2H), 7.40-7.30 (m, 3H), 6.89-6.62 (br s, 2H), 4.73 (s, 2H).

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-04878aead7534e9e9739577f7aea1db0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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