2,4-Dichloro-5-fluoropyrimidine → HCID 66758256, compound

HRID 1724355Notes

Reaction equation

HRID 1724355 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]([CH:14]=[C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([NH2:18])[CH2:16]1)=[O:13]>>[CH3:10][O:11][C:12]([CH:14]=[C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([NH:18][C:2]2[N:7]=[C:6]([NH:18][C:17]3[CH2:16][C:15](=[CH:14][C:12]([O:11][CH3:10])=[O:13])[CH:21]=[CH:20][CH:19]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH2:16]1)=[O:13]

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 66758734HCID 66758734, compound

Product 1

HCID 66758256HCID 66758256, compound

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 2,4-dichloro-5-fluoropyrimidine and 3-(methoxycarbonylmethylene)aniline were reacted to produce the desired N2,N4-bis(3-methoxycarbonylmethylenephenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 10.23 (br s, 1H), 10.05 (br s, 1H), 8.26 (d, 1H, J=4.6 Hz), 7.64 (d, 1H, J=8.2 Hz), 7.51 (br s, 1H), 7.46 (d, 1H, J=8.2 Hz), 7.33 (br s, 1H), 7.29 (t, 1H, J=7.6 Hz), 7.20 (t, 1H, J=7.6 Hz), 7.06 (d, 1H, J=7.6 Hz), 6.93 (d, 1H, J=7.6 Hz), 3.63 (s, 2H), 3.58 (s, 3H), 3.57 (s, 3H), 3.56 (s, 2H); LCMS: ret. time: 21.74 min.; purity: 92%; MS (m/e): 425 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-64d497e898814dffb4cd2dc1537082c7
Source dataset
uspto-grants-2009_02
Patent number
US07485724B2

Reaction notes

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