3-Chloroaniline → N-(3-chlorophenyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine

HRID 2214778Notes

Reaction equation

HRID 2214778 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>>[Cl:22][C:23]1[CH:24]=[C:25]([NH:26][C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][N:6]=2)[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 79323-ChloroanilineHCID 219484652-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine

Product 1

HCID 9950177N-(3-chlorophenyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(methylsulfonyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidine (1-7, 96 mg) and 3-chloroaniline (0.5 mL, excess) was heated at 100° C. for 24 hours. The residue was purified by flash column chromatography (hexanes, initially, grading to 40% hexanes in ethyl acetate) to give N-(3-chlorophenyl)-4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-amine (1-8) as an off-white foam. 1H NMR (300 MHz, CDCl3) δ 8.37 (d, 1H, J=5.2 Hz), 7.78 (d, 1H, J=1.8 Hz), 7.56 (m, 1H), 7.46–7.32 (m, 5H), 7.12 (m, 1H), 7.08 (m, 1H), 6.96 (m, 1H), 6.92 (d, 1H, J=1.8 Hz), 6.66 (d, 1H, J=5.2 Hz).

Workup

  1. customThe residue was purified by flash column chromatography (hexanes

Sources & evidence

ORD record
ord-8f4454d6ac6f403591187a9da89ba283
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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