1,4-Benzodioxan-6-ylamine → HCID 22060605, compound

HRID 1474918Notes

Reaction equation

HRID 1474918 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:11]C3C(F)=CN=C(NC4C=CC=C(O)C=4)N=3)=[CH:4][C:3]=2[O:2]1.[Br:27][C:28]1[C:29]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)=[N:30][C:31](Cl)=[N:32][CH:33]=1.C1COC2C=CC(N)=CC=2O1>>[Br:27][C:28]1[C:29]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)=[N:30][C:31]([NH:11][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:10][CH2:1][O:2][C:3]=3[CH:4]=2)=[N:32][CH:33]=1

Participants

4

Reactant 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 22060529HCID 22060529, compound

Product 1

HCID 22060605HCID 22060605, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 5-bromo-2-chloro-N4-(3-hydroxyphenyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield 5-bromo-N2-(3,4-ethylenedioxyphenyl)-N4-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 9.33 (s, 1H), 9.06 (s, 1H), 8.34 (s, 1H), 8.14 (s, 1H), 7.13-7.06-(m, 4H), 6.94 (bs, 1H), 6.61 (d, 1H, J=8.7 Hz), 6.54-6.50 (m, 1H), 4.17-4.13 (m, 4H); LCMS: ret. time: 20.01 min.; purity: 93%; MS (m/e): 416 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-d37b6e31c75b4621805cb3eda0ba9ec3
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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