3-Nitroaniline → 4-(3-Nitroanilino)-6-methyl-2-(2-pyridinyl)pyrimidine

HRID 1765145Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])([O-:17])=[O:16]>>[N+:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH:21][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1)([O-:17])=[O:16]

Participants

Reactant 2

HCID 74233-Nitroaniline

HCID 27633954-Chloro-6-methyl-2-(pyridin-2-yl)pyrimidine

Product 1

HCID 227323934-(3-Nitroanilino)-6-methyl-2-(2-pyridinyl)pyrimidine

Procedure

The title compound was prepared from 4-chloro-6-methyl-2-(2-pyridinyl)pyrimidine (50 mg, 0.243 mmol) and 3-nitroaniline (34 mg, 0.243 mmol) similar to Example 11 as a yellow solid (65 mg, 87%). 1H NMR (DMSO-d6): 10.17 (s, 1H), 9.18 (s, 1H), 8.77 (d, J=4.8 Hz, 1H), 8.39 (d, J=8.1 Hz, 1H), 8.13 (d, J=7.2 Hz, 1H), 7.98 (t, J=6.9 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.63 (t, J=8.3 Hz, 1H), 7.55–7.51 (m, 1H), 6.74 (s, 1H), 2.47 (s, 3H).

Sources & evidence

ORD record: ord-01c7feca6066499d8803b274de68d5c0
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226927B2

Reaction notes

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