5-Amino-2-chloropyridine → 2-chloro-N4-(6-chloropyridin-3-yl)-5-fluoro-4-pyrimidineamine

HRID 76415

Reaction equation

HRID 76415 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1>>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:12]=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 793055-Amino-2-chloropyridineHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 220602542-chloro-N4-(6-chloropyridin-3-yl)-5-fluoro-4-pyrimidineamine

Procedure

In like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine the reaction of 2,4-dichloro-5-fluoropyrimidine with 3-amino-6-chloropyridine gave 2-chloro-N4-(6-chloropyridin-3-yl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.53 (d, 1H, J=3 Hz), 8.25 (dd, 1H, J=3 and 9 Hz), 8.15 (d, 1H, J=2.4 Hz), 7.39 (d, 1H, J=8.7 Hz), 7.00 (bs, 1H); LCMS: purity: 98%; MS (m/e): 259 (M+).

Workup

  1. customIn like manner to the preparation of 2-chloro-5-fluoro-N4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyrimidineamine

Sources & evidence

ORD record
ord-b648684101bd4be2b8ad21afbb819101
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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