2,4-Dichloro-5-fluoropyrimidine → HCID 22060767, compound

HRID 1483365Notes

Reaction equation

HRID 1483365 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9].Cl[C:13]1[N:18]=[C:17](Cl)[C:16]([F:20])=[CH:15][N:14]=1>>[OH:11][C:4]1[CH:5]=[CH:6][C:7]([CH:8]([CH3:9])[CH3:10])=[C:2]([NH:1][C:13]2[N:18]=[C:17]([NH:1][C:2]3[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=3[CH:8]([CH3:10])[CH3:9])[C:16]([F:20])=[CH:15][N:14]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 36141583-Amino-4-isopropylphenol

Product 1

HCID 22060767HCID 22060767, compound

Procedure

In like manner to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, 3-amino-4-isopropylphenol and 2,4-dichloro-5-fluoropyrimidine were reacted to produce N2,N4-bis(5-hydroxy-2-isopropylphenyl)-5-fluoro-2,4-pyrimidinediamine. 1H NMR (CDCl3): δ 7.93 (d, 1H, J=3.5 Hz), 7.79 (br s, 1H), 7.64 (br s, 1H), 7.13 (d, 1H, J=8.7 Hz), 7.06 (d, 1H, J=2.3 Hz), 7.05 (d, 1H, J=8.7 Hz), 6.89 (d, 1H, J=2.3 Hz), 6.66 (d, 1H, J=2.3 and 8.7 Hz), 6.57 (d, 1H, J=2.3 and 8.7 Hz), 2.96 (m, 2H), 1.25 (d, 6H, J=7.0 Hz), 1.13 (dd, 6H, J=7.0 Hz); LCMS: ret. time: 24.27 min.; purity: 97%; MS (m/e): 397 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-893336799f4347c2b28e665eddfc05a7
Source dataset
uspto-grants-2016_08
Patent number
US09416112B2

Reaction notes

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