Methylamine hydrochloride → HCID 66759113, compound

HRID 1829466Notes

Reaction equation

[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[N:17]=[C:16]([NH:18][C:19]4[CH:20]=[CH:21][C:22]5[O:26][C:25]([C:27]([O:29]C)=O)=[CH:24][C:23]=5[CH:31]=4)[C:15]([F:32])=[CH:14][N:13]=3)=[CH:4][C:3]=2[O:2]1.Cl.[CH3:34][NH2:35]>>[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11][C:12]3[N:17]=[C:16]([NH:18][C:19]4[CH:20]=[CH:21][C:22]5[O:26][C:25]([C:27]([NH:35][CH3:34])=[O:29])=[CH:24][C:23]=5[CH:31]=4)[C:15]([F:32])=[CH:14][N:13]=3)=[CH:4][C:3]=2[O:2]1

Participants

Reactant 2

HCID 6364545Methylamine hydrochloride

HCID 66759548HCID 66759548, compound

Product 1

HCID 66759113HCID 66759113, compound

Procedure

In like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine, the reaction of N2-(3,4-ethylenedioxyphenyl)-N4-(2-methoxycarbonylbenzofuran-5-yl)-5-fluoro-2,4-pyrimidinediamine with methylamine hydrochloride gave N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-[2-(N-methylamino)carbonylbenzofuran-5-yl]-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 8.10 (s, 1H), 7.94 (d, 1H, J=5.1 Hz), 7.59 (s, 2H), 7.44 (s, 1H), 6.96 (d, 1H, J=2.4 Hz), 6.82 (d, 1H, J=8.4 Hz), 6.76 (dd, 1H, J=3.6 and 8.1 Hz), 4.22 (s, 2H), 4.21 (s, 2H), 2.95 (s, 3H); LCMS: ret. time: 17.76 min.; purity: 97%; MS (m/e): 436 (MH+).

Workup

customIn like manner to the preparation of N4-(ethylenedioxyphenyl)-5-fluoro-N2-[3-(N-methylamino)carbonylmethyleneoxyphenyl]-2,4-pyrimidinediamine

Sources & evidence

ORD record: ord-98c82ae981794c38922fb08260c0a167
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060827B2

Reaction notes

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