2-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine → HCID 22060368, compound

HRID 733970Notes

Reaction equation

HRID 733970 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]3[O:15][CH2:16][CH2:17][O:18][C:11]=3[CH:10]=2)[C:5]([F:19])=[CH:4][N:3]=1.[Cl:20][C:21]1[N:22]=[C:23](N)[NH:24][C:25]=1[Cl:26]>>[Cl:26][C:25]1[N:24]=[CH:23][N:22]([C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:14]=[CH:13][C:12]5[O:15][CH2:16][CH2:17][O:18][C:11]=5[CH:10]=4)[C:5]([F:19])=[CH:4][N:3]=3)=[CH:10][CH:11]=2)[C:21]=1[Cl:20]

Participants

3

Reactant 2

HCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamineHCID 66759668HCID 66759668, compound

Product 1

HCID 22060368HCID 22060368, compound

Procedure

In like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, the reaction of 2-chloro-N4-(3,4-ethlenedioxyphenyl)-5-fluoro-4-pyrimidineamine with 4,5-dichloro-1H-imidazoleamine gave N2-[4-(4,5-dichloro-1H-imidazol-1-yl)phenyl]-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.10 (s, 1H), 9.85 (s, 1H), 8.20 (d, 1H, J=4.2 Hz), 8.01 (s, 1H), 7.78 (d, 1H, J=8.7 Hz), 7.36 (d, 1H, J=9 Hz), 7.25 (d, 1H, J=3 Hz), 7.14 (dd, 1H, J=2.1 and 9 Hz), 6.85 (d, 1H, J=8.7 Hz); LCMS: ret. time: 23.59 min.; purity: 95%; MS (m/e): 474 (MH+).

Workup

  1. customIn like manner to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine

Sources & evidence

ORD record
ord-b16a6a02a6094eb1ab9819c229377561
Source dataset
uspto-grants-2009_09
Patent number
US07589200B2

Reaction notes

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