1H-Indole-2-carboxylic acid, 7-amino-, ethyl ester → N4-(3,5-dimethoxyphenyl)-N2-(2-ethoxycarbonylindol-7-yl)-5-fluoro-2,4-pyrimidinediamine

HRID 405481Notes

Reaction equation

HRID 405481 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([O:17][CH3:18])[CH:10]=2)[C:5]([F:19])=[CH:4][N:3]=1.[CH2:20]([O:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][C:28]=2[NH2:34])=[O:24])[CH3:21]>>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[C:5]([F:19])=[CH:4][N:3]=[C:2]([NH:34][C:28]3[CH:29]=[CH:30][CH:31]=[C:32]4[C:27]=3[NH:26][C:25]([C:23]([O:22][CH2:20][CH3:21])=[O:24])=[CH:33]4)[N:7]=2)[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=1

Participants

3

Reactant 2

HCID 111381941H-Indole-2-carboxylic acid, 7-amino-, ethyl esterHCID 220606942-chloro-N4-(3,5-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine

Product 1

HCID 22060274N4-(3,5-dimethoxyphenyl)-N2-(2-ethoxycarbonylindol-7-yl)-5-fluoro-2,4-pyrimidinediamine

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-(3,5-dimethoxyphenyl)-5-fluoro-4-pyrimidineamine with 2-ethoxycarbonyl-7-aminoindole gave N4-(3,5-dimethoxyphenyl)-N2-(2-ethoxycarbonylindol-7-yl)-5-fluoro-2,4-pyrimidinediamine. LCMS: ret. time: 24.21 min.; purity: 91%; MS (m/e): 452 (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-f1aad0fd17744f708b36941c6ba6745c
Source dataset
uspto-grants-2014_06
Patent number
US08748597B2

Reaction notes

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