2,4-Dichloro-5-fluoropyrimidine → HCID 22061183, compound

HRID 1960715Notes

Reaction equation

HRID 1960715 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[O:14][CH2:15][CH2:16][OH:17]>>[OH:17][CH2:16][CH2:15][O:14][C:13]1[CH:12]=[C:11]([NH:10][C:2]2[N:7]=[C:6]([NH:10][C:11]3[CH:20]=[CH:19][CH:18]=[C:13]([O:14][CH2:15][CH2:16][OH:17])[CH:12]=3)[C:5]([F:9])=[CH:4][N:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 39448452-(3-aminophenoxy)ethanol

Product 1

HCID 22061183HCID 22061183, 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 2-(3-aminophenoxy)ethanol were reacted to produce N2,N4-bis[3-(2-hydroxyethoxy)phenyl]-5-fluoro-2,4-pyrimidinediamine. 1H NMR (DMSO-d6): δ 9.50 (br s, 1H), 9.35 (br s, 1H), 8.13 (d, 1H, J=4.1 Hz), 7.44 (d, 1H, J=7.6 Hz), 7.26-7.19 (m, 4H), 7.10 (t, 1H, J=7.6 Hz), 6.65 (dd, 1H, J=2.3 and 8.2 Hz), 6.50 (dd, 1H, J=2.3 and 8.2 Hz), 5.0 (br s, 2H), 3.91 (t, 2H, J=5.2 Hz), 3.85 (t, 2H, J=5.2 Hz), 3.68 (qt, 2H, J=5.2 Hz), 3.66 (qt, 2H, J=5.2 Hz); LCMS: ret. time: 15.76 min.; purity: 97%; MS (m/e): 401 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-61e6d98b537a431e8f64c13bb2629589
Source dataset
uspto-grants-2013_04
Patent number
US08410266B2

Reaction notes

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