2,4-Dichloro-5-fluoropyrimidine → N2,N4-bis(4-benzyloxy-3-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1829331Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH2:10]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][C:19]=1[C:25]([F:28])([F:27])[F:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO.O>[CH2:10]([O:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[N:7]=[C:6]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([O:17][CH2:10][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[C:19]([C:25]([F:26])([F:27])[F:28])[CH:20]=3)[C:5]([F:9])=[CH:4][N:3]=2)=[CH:20][C:19]=1[C:25]([F:26])([F:27])[F:28])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2,4-Dichloro-5-fluoropyrimidine (50 mg, 0.30 mmol) was dissolved in a mixture of MeOH (1 ml) and H2O (0.1 ml). 4-benzyloxy-3-trifluoromethylaniline (481 mg, 1.8 mmol) was added and the mixture was refluxed for 2 days (70° C. oil-bath temperature). The mixture was cooled to 22° C., concentrated to dryness under reduced pressure and subjected to column chromatography on silica gel (CHCl3-Acetone, 9:1) to give N2,N4-bis(4-benzyloxy-3-trifluoromethylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.51 (s, 1H), 8.05 (s, 1H), 7.38–7.64 (m, 5H), 6.94–7.14 (m, 11H), 6.44–6.73 (m, 4H), 4.84 (s, 2H), 4.79 (s, 2H); LCMS purity: 94.7%; MS (m/e): 628.93 (M+, 100).

Workup

temperatureThe mixture was cooled to 22° C.
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-f607db4a5637487685b4c8741e5e993f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060827B2

Reaction notes

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