5-Chloro-2-methoxyphenylboronic acid → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(5-chloro-2-methoxyphenyl)pyrimidine-2,4-diamine

HRID 2386989Notes

Reaction equation

HRID 2386989 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16](Cl)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25](B(O)O)[CH:26]=1>>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([C:23]3[CH:22]=[C:21]([Cl:20])[CH:26]=[CH:25][C:24]=3[O:30][CH3:31])[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 71681979N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-chloropyrimidine-2,4-diamine

Product 1

HCID 44609563N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(5-chloro-2-methoxyphenyl)pyrimidine-2,4-diamine

Procedure

The product of Example 6A (50 mg, 0.178 mmol) and 5-chloro-2-methoxyphenyl boronic acid (37 mg, 0.196 mmol) were treated under the conditions described in Example 6B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.85 (d, J=2.78 Hz, 1H) 7.61 (d, J=5.55 Hz, 1H) 7.39 (dd, J=8.92, 2.97 Hz, 1H) 7.12 (d, J=8.73 Hz, 1H) 7.02 (s, 1H) 6.88 (s, 1H) 6.42 (s, 1H) 5.97 (s, 2H) 5.86 (s, 2H) 5.74 (d, 1H) 3.82 (s, 3H) 3.34-3.43 (m, 4H); MS (ESI+) m/z 387.2 (M+H)+.

Sources & evidence

ORD record
ord-f793b0e5d07b479c9eaecd0f8cb1104e
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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