2,4-Dichloro-5-fluoropyrimidine → N2,N4-bis(4-ethoxycarbonylamino-3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 1724311Notes

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

Participants

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidine

HCID 4078585ethyl N-(4-amino-2-hydroxyphenyl)carbamate

Product 1

HCID 22060292N2,N4-bis(4-ethoxycarbonylamino-3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

Procedure

In like manner to N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 4-ethoxycarbonylamino-3-hydroxyaniline were reacted to yield N2,N4-bis(4-ethoxycarbonylamino-3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CD3OD): δ 7.86 (d, 1H J=4 Hz), 7.67 (m, 2H), 7.20 (dd, 1H, J=8 Hz, J=4.1 Hz), 7.13 (d, 1H), 6.90 (m, 2H), 4.2(m, 4H), 1.32 (m, 6H); LCMS: ret. time: 20.92 min.; purity: 98%; MS (m/e): 487 (MH+).

Sources & evidence

ORD record: ord-e0627299ac734834bb512a9f873c52a2
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485724B2

Reaction notes

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