2,4-Dichloro-5-fluoropyrimidine → N2,N4-bis(2-ethoxycarbonylindol-5-yl)-5-fluoro-2,4-pyrimidinediamine

HRID 71390Notes

Reaction equation

HRID 71390 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH2:10]([O:12][C:13]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([NH2:24])=[CH:19][CH:18]=2)=[O:14])[CH3:11]>>[CH2:10]([O:12][C:13]([C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][C:20]([NH:24][C:2]1[N:7]=[C:6]([NH:24][C:20]3[CH:21]=[C:22]4[C:17](=[CH:18][CH:19]=3)[NH:16][C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:23]4)[C:5]([F:9])=[CH:4][N:3]=1)=[CH:19][CH:18]=2)=[O:14])[CH3:11]

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylate

Product 1

HCID 22060513N2,N4-bis(2-ethoxycarbonylindol-5-yl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 2-ethoxycarbonyl-5-indoleamine were reacted to yield N2,N4-bis(2-ethoxycarbonylindol-5-yl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 11.83 (s, 1H), 11.63 (s, 1H), 9.21 (s, 1H), 8.99 (s, 1H), 8.08 (s, 1H), 8.01 (m, 2H), 7.49-7.22 (m, 4H), 6.92 (s, 1H), 6.63 (s, 1H), 4.29 (q, 4H, J=7.2 Hz), 1.32 (m, 6H); LCMS: ret. time: 24.74 min.; purity: 99%; MS (m/e): 503 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f89a0a6127314778b72af82a620f6281
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Reaction notes

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