2-Chloropyrimidine → 5-[3-Fluoro-2'-(pyrimidin-2-ylsulfanyl)biphenyl-4-yl]pyrimidin-2-amine hydrochloride

HRID 1523895Notes

Reaction equation

HRID 1523895 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][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])=[CH:4][N:3]=1.[Cl:22][C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1>>[ClH:22].[F:21][C:9]1[CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20][C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 744042-ChloropyrimidineHCID 903131044'-(2-Aminopyrimidin-5-yl)-5'-fluorobiphenyl-2-thiol

Product 1

HCID 903134065-[3-Fluoro-2'-(pyrimidin-2-ylsulfanyl)biphenyl-4-yl]pyrimidin-2-amine hydrochloride

Procedure

The title compound was prepared using analogous conditions to those described in Example 213 utilizing 4′-(2-aminopyrimidin-5-yl)-3′-fluoro-[1,1′-biphenyl]-2-thiol and 2-chloropyrimidine. MS (ESI): mass calcd. for C20H14FN5S, 375.10; m/z found, 375.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.66 (s, 2H), 8.56 (d, J=4.9, 2H), 7.79-7.73 (m, 1H), 7.63-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.33-7.24 (m, 2H), 7.21 (m, 1H), 6.23 (s, 2H).

Sources & evidence

ORD record
ord-a824afc2408a45428b2964b429578ab2
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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