1,4-Benzodioxan-6-ylamine → HCID 178514821, compound

HRID 1163808Notes

Reaction equation

HRID 1163808 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([B:15]([OH:17])O)[CH:10]=2)[C:5]([F:18])=[CH:4][N:3]=1.[CH2:19]1[CH2:29][O:28][C:27]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=2[O:20]1>>[CH2:19]1[CH2:29][O:28][C:27]2[CH:26]=[CH:25][C:23]([NH:24][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([BH:15][OH:17])[CH:10]=4)[C:5]([F:18])=[CH:4][N:3]=3)=[CH:22][C:21]=2[O:20]1

Participants

3

Reactant 2

HCID 891481,4-Benzodioxan-6-ylamineHCID 22060894HCID 22060894, compound

Product 1

HCID 178514821HCID 178514821, compound

Procedure

In a like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-5-fluoro-N4-(3-dihydroxyborylphenyl)-4-pyrimidineamine and 3,4-ethylenedioxyaniline were reacted to produce N2-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-(3-hydroxyborylphenyl)-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.46 (bs, 1H), 9.11 (bs, 1H), 8.05 (d, 1H, J=4.2 Hz), 7.95 (bs, 1H), 7.88 (s, 1H), 7.78 (d, 1H, J=7.5 Hz), 7.52 (d, 1H, J=7.5 Hz), 7.29 (t, 1H, J=7.5 Hz), 7.16 (s, 1H), 7.02 (d, 1H, J=8.7 Hz), 6.65 (d, 1H, J=8.7 Hz), 3.40 (s, 4H); LCMS: purity: 98%; MS (m/e): 383(MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-cd32e59ff14447998f70a410a16fbfba
Source dataset
uspto-grants-2010_10
Patent number
US07820819B2

Reaction notes

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