4-Aminobenzyl alcohol → 2-chloro-5-fluoro-N4-[4-(hydroxymethyl)phenyl]4-pyrimidineamine

HRID 578196Notes

Reaction equation

HRID 578196 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1>>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 693314-Aminobenzyl alcoholHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 220604802-chloro-5-fluoro-N4-[4-(hydroxymethyl)phenyl]4-pyrimidineamine

Procedure

In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 4-aminobenzylalcohol were reacted to yield 2-chloro-5-fluoro-N4-[4-(hydroxymethyl)phenyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.08 (d, 1H, J=2.7 Hz), 7.62 (d, 2H, J=9.0 Hz), 7.40 (d, 2H, J=8.1 Hz), 6.99 (bs, 1H), 4.70 (s, 2H); 19F NMR (CDCl3): −44570 (s, 1F); LCMS: ret. time: 19.57 min.; purity: 99%; MS (m/e): 254 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-eadbebaa09694257a53b008393f5a687
Source dataset
uspto-grants-2015_05
Patent number
US09040550B2

Reaction notes

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