Styrylboronic acid → N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-[(E)-2-phenylvinyl]pyrimidine-2,4-diamine

HRID 2386990Notes

Reaction equation

HRID 2386990 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.[CH:20](/B(O)O)=[CH:21]\[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:15]=[C:14]([NH2:19])[N:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 5702628Styrylboronic acidHCID 71681979N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-chloropyrimidine-2,4-diamine

Product 1

HCID 44609564N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-6-[(E)-2-phenylvinyl]pyrimidine-2,4-diamine

Procedure

The product of Example 6A (57 mg, 0.203 mmol) and (E)-styrylboronic acid (33 mg, 0.223 mmol) were treated under the conditions described in Example 6B to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.48-7.65 (m, 4H) 7.26-7.43 (m, 3H) 6.76-7.02 (m, J=15.86 Hz, 3H) 5.80-5.94 (m, 5H) 5.74 (d, J=5.95 Hz, 1H) 3.34-3.43 (m, 4H); MS (ESI+) m/z 349.0 (M+H)+.

Sources & evidence

ORD record
ord-24e2a32340d04484967c4298a3714f6f
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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