4-Chloropyrimidin-5-amine → 4-{[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]sulfanyl}pyrimidin-5-amine hydrochloride

HRID 1523848Notes

Reaction equation

HRID 1523848 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([SH:20])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:21])=[N:6][CH:7]=1.[NH2:22][C:23]1[C:24]([Cl:29])=[N:25][CH:26]=[N:27][CH:28]=1>>[ClH:29].[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:20][C:24]3[C:23]([NH2:22])=[CH:28][N:27]=[CH:26][N:25]=3)=[CH:10][C:9]=2[F:21])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 134045414-Chloropyrimidin-5-amineHCID 1364991434'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-thiol

Product 1

HCID 903137414-{[4'-(5-Aminopyrazin-2-yl)-3'-fluorobiphenyl-2-yl]sulfanyl}pyrimidin-5-amine hydrochloride

Procedure

The title compound was prepared using analogous conditions to those described in Example 213 utilizing 4′-(5-aminopyrazin-2-yl)-3′-fluoro-[1,1′-biphenyl]-2-thiol and 5-amino-4-chloropyrimidine. MS (ESI): mass calcd. for C20H15FN6S, 390.11; m/z found, 391.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.35-8.30 (m, 1H), 8.22 (s, 1H), 8.02 (d, J=1.4, 1H), 7.90 (s, 1H), 7.80 (m, 1H), 7.59-7.54 (m, 2H), 7.52-7.44 (m, 2H), 7.24 (dd, J=6.5, 1.6, 1H), 7.21 (m, 1H).

Sources & evidence

ORD record
ord-234afd88a5f04924bdf74aa0c2d4ab79
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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