4-(1-Aminoethyl)phenol → (+)-2-chloro-5-fluoro-N4-[1-(4-hydroxyphenyl)ethyl]-4-pyrimidineamine

HRID 534292Notes

Reaction equation

HRID 534292 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([NH2:19])[CH3:18])=[CH:13][CH:12]=1>>[Cl:1][C:2]1[N:7]=[C:6]([NH:19][CH:17]([C:14]2[CH:15]=[CH:16][C:11]([OH:10])=[CH:12][CH:13]=2)[CH3:18])[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 1235944-(1-Aminoethyl)phenolHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 22061104(+)-2-chloro-5-fluoro-N4-[1-(4-hydroxyphenyl)ethyl]-4-pyrimidineamine

Procedure

In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with 1-(4-hydroxyphenyl)ethylamine to provide (±)-2-chloro-5-fluoro-N4-[1-(4-hydroxyphenyl)ethyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 7.88 (d, 1H, J=2.3 Hz), 7.50-7.47 (dd, 2H, J=1.7 and 8.7 Hz), 7.26-7.23 (dd, J=8.7 and 1.7 Hz), 5.35-5.28 (m, 2H), 1.59 (d, 3H, J=7.0 Hz).

Sources & evidence

ORD record
ord-aed418308b864f4f80009f20b32ce628
Source dataset
uspto-grants-2014_10
Patent number
US08853397B2

Reaction notes

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