3-Aminophenol → HCID 22060335, compound

HRID 1960760Notes

Reaction equation

HRID 1960760 reaction equation
C1COC2C=[CH:6][C:5]([NH:11][C:12]3[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=4)[N:13]=3)=CC=2O1.ClC1N=C(NCC[S:37][CH2:38][C:39]2[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:46])C(F)=CN=1.NC1C=C(O)C=CC=1>>[Cl:46][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]([F:45])[C:39]=1[CH2:38][S:37][CH2:6][CH2:5][NH:11][C:12]1[C:17]([F:18])=[CH:16][N:15]=[C:14]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[N:13]=1

Participants

4

Reactant 3

HCID 115683-AminophenolHCID 22060334N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-primidinediamineHCID 220611812-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine

Product 1

HCID 22060335HCID 22060335, compound

Procedure

In a manner similar to the preparation of N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine, 2-chloro-N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-4-pyrimidineamine and 3-aminophenol were reacted to yield N4-[2-[(2-chloro-6-fluorobenzyl)thio]ethyl]-5-fluoro-N2-(3-hydroxyphenyl)-2,4-pyrimidinediamine. 1H NMR (methyl sulfoxide-d6): δ 9.76 (bs, 1H), 9.42 (bs, 1H), 8.70 (bs, 1H), 8.02 (d, 1H, J=5.1 Hz), 7.33-7.30 (m, 2H), 7.24-7.18 (m, 1H), 7.08-6.96 (m, 2H), 6.42 (d, 1H, J=4.6 Hz), 3.82 (d, 2H, J=1.2 Hz), 3.68-3.61 (m, 2H), 2.77 (t, 2H, J=7.2 Hz); LCMS: ret. time: 23.00 min.; purity: 93%; MS (m/e): 424 (MH+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0b7b771d21454aec846d717ba89f0331
Source dataset
uspto-grants-2013_04
Patent number
US08410266B2

Reaction notes

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