1,4-Benzodioxan-6-ylamine → HCID 66759190, compound

HRID 1829366Notes

Reaction equation

HRID 1829366 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.Cl[C:28]1[N:33]=[C:32]([NH:34][CH:35]([C:42]([O:44][CH3:45])=[O:43])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:31]([C:46]#[N:47])=[CH:30][N:29]=1.C1COC2C=CC(N)=CC=2O1>>[C:46]([C:31]1[C:32]([NH:34][CH:35]([C:42]([O:44][CH3:45])=[O:43])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][C:28]([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:29][CH:30]=1)#[N:47]

Participants

4

Reactant 3

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220605702-chloro-5-cyano-N4-(methoxycarbonylbenzyl)-4-pyrimidineamine

Product 1

HCID 66759190HCID 66759190, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-cyano-N4-(methoxycarbonylbenzyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to yield 5-cyano-N2-(3,4-ethylenedioxyphenyl)-N4-(methoxycarbonylbenzyl)-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 8.23 (s, 1H), 7.41–7.32 (m, 5H), 7.01 (d, 1H, J=3.0 Hz), 6.86–6.71 (m, 3H), 6.54 (bs, 1H), 5.48 (d, 1H, J=6.3 Hz), 4.31 (bs, 4H), 3.68 (s, 3H); LCMS: ret. time: 25.53 min.; purity: 97%; MS (m/e): 418 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-23349cb64f1e46c8b1e34fb0127b06d4
Source dataset
uspto-grants-2006_06
Patent number
US07060827B2

Reaction notes

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