3,5-Dichlorophenylboronic acid → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3,5-dichlorophenyl)pyrimidine-2,4-diamine

HRID 2386988Notes

Reaction equation

HRID 2386988 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]=[C:23](B(O)O)[CH:24]=[C:25]([Cl:27])[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]=[C:25]([Cl:27])[CH:24]=3)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 71681979N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-chloropyrimidine-2,4-diamine

Product 1

HCID 44609413N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-(3,5-dichlorophenyl)pyrimidine-2,4-diamine

Procedure

The product of Example 6A (62 mg, 0.221 mmol) and 3,5-dichlorophenyl boronic acid (46 mg, 0.243 mmol) were treated under the conditions described in Example 6B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (s, 2H) 7.66 (t, J=2.03 Hz, 1H) 7.61 (d, J=5.76 Hz, 1H) 6.99 (s, 1H) 6.86 (s, 1H) 6.33 (s, 1H) 6.15 (s, 2H) 5.85 (s, 2H) 5.74 (d, J=5.76 Hz, 1H) 3.33-3.51 (m, 4H); MS (ESI+) m/z 390.9 (M+H)+.

Sources & evidence

ORD record
ord-3bb4cef7710d41c9af1f10a886c9f178
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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