1,4-Benzodioxan-6-ylamine → HCID 22060321, compound

HRID 1990471Notes

Reaction equation

HRID 1990471 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[C:5]([F:23])=[CH:4][N:3]=1.[CH2:24]1[CH2:34][O:33][C:32]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=2[O:25]1>>[CH2:21]([O:20][C:18]([C:15]([CH3:17])([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[C:5]([F:23])=[CH:4][N:3]=[C:2]([NH:29][C:28]3[CH:30]=[CH:31][C:32]4[O:33][CH2:34][CH2:24][O:25][C:26]=4[CH:27]=3)[N:7]=2)=[CH:10][CH:11]=1)=[O:19])[CH3:22]

Participants

3

Reactant 2

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060453HCID 22060453, compound

Product 1

HCID 22060321HCID 22060321, compound

Procedure

In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro -N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-5-fluoro-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to produce N4-[4-[ethoxycarbonyl(dimethyl)methyl]phenyl]-N2-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.31 (s, 1H), 8.97 (s, 1H), 8.03 (d, 1H, J=3.5 Hz), 7.70 (d, 2H, J=8.8 Hz), 7.29 (d, 1H, J=2.3 Hz), 7.23 (d, 2H, J=8.8 Hz), 6.98 (dd, 1H, J=2.1 and 8.8 Hz), 6.66 (d, 1H, J=8.2 Hz), 4.19-4.15 (m, 4H), 4.07 (qt, 2H, J=7.0 Hz), 1.48 (s, 6H), 1.10 (t, 3H, J=7.0 Hz). LCMS: ret. time: 24.51 min.; purity: 100%; MS (m/e): 453 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-92cbb13756a84cf1b8c1a82301a8163d
Source dataset
uspto-grants-2010_01
Patent number
US07642351B2

Reaction notes

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