Triethylamine → 2-Chloro-N-[3-(phenylmethoxy)phenyl]-4-pyrimidinamine

HRID 1474768Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2,6-dichloropyrimidine (2.00 g, 13.4 mmol), 3-benzyloxyaniline (2.07 g, 13.4 mmol) and triethylamine (2.72 g, 26.8 mmol) in 1-butanol (20 mL) was stirred at 50° C. for 17 h. The reaction mixture was concentrated to remove most of the 1-butanol, the crude product was preabsorbed onto silica gel using chloroform and purified by flash chromatography (95:5 chloroform/methanol) to afford N4-(3-benzyloxyphenyl)-2-chloro-4-pyrimidineamine (1.70 g, 40%) as colorless oil: 1H NMR (300 MHz, DMSO-d6) δ 10.2 (s, 1H), 8.16 (d, J=6.0 Hz, 1H), 7.48-7.24 (m, 7H), 7.12 (d, J=9.0 Hz, 1H), 6.78 (m, 2H), 5.11 (s, 2H); ESI MS m/z 312 [C17H14ClN3O+H]+.

Workup

concentrationThe reaction mixture was concentrated
customto remove most of the 1-butanol
customthe crude product was preabsorbed onto silica gel
custompurified by flash chromatography (95:5 chloroform/methanol)

Sources & evidence

ORD record: ord-223842c4fed146b29fef2bfa44636298
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018204B1

Reaction notes

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