2-Amino-o-cresol → N2,N4-bis(3-hydroxy-2-methylphenyl)-5-fluoro-2,4-pyrimidinediamine

HRID 71413

Reaction equation

HRID 71413 reaction equation
OC1C=C(N[C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[C:12]([F:23])=[CH:11][N:10]=2)C=CC=1.[OH:24][C:25]1[C:26]([CH3:32])=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28].Cl[C:34]1N=C(Cl)C(F)=CN=1>>[OH:24][C:25]1[C:26]([CH3:32])=[C:27]([NH:28][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]=3[CH3:34])[C:12]([F:23])=[CH:11][N:10]=2)[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 1044482-Amino-o-cresolHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 9904854R-112

Product 1

HCID 22060942N2,N4-bis(3-hydroxy-2-methylphenyl)-5-fluoro-2,4-pyrimidinediamineYield 88%

Procedure

In a manner analogous to the preparation of N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine, the reaction of 3-hydroxy-2-methylaniline (369 mg, 3 mmol) and 2,4-dichloro-5-fluoropyrimidine (100 mg, 0.6 mmol) gave N2,N4-bis(3-hydroxy-2-methylphenyl)-5-fluoro-2,4-pyrimidinediamine (180 mg, 88%). 1H NMR (acetone-d6): δ 2.14 (s, 3 H), 2.22 (s, 3 H), 6.61 (d, J=8.1 Hz, 1 H), 6.78 (t, J=8.7 Hz, 1 H), 6.87 (d, J=7.8 Hz, 1 H), 6.99 (d, J=9.0 Hz, 1 H), 7.08 (t, J=7.8 Hz, 1 H), 7.13 (dd, J=3.9, 8.4 Hz, 1 H), 8.24 (d, J=5.1 Hz, 1 H), 8.32 (br, 1 H, NH), 8.57 (br, 1 H, NH); LCMS: ret. time: 16.51 min.; purity: 90.47%; MS (m/e): 341.07 (MH+).

Sources & evidence

ORD record
ord-5e847c96b0f949e7b423496f7b034cd3
Source dataset
uspto-grants-2014_09
Patent number
US08822685B2

Linked notes

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