2-Chloro-4-aminopyrimidine → N4-{2-[(4-aminopyrimidin-2-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

HRID 2386984Notes

Reaction equation

HRID 2386984 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:8]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:9]=2[N:10]=[C:11]([NH2:13])[N:12]=1.[NH2:23][C:24]1[N:29]=[C:28](Cl)[N:27]=[CH:26][CH:25]=1>>[NH2:23][C:24]1[CH:25]=[CH:26][N:27]=[C:28]([NH:3][CH2:4][CH2:5][NH:6][C:7]2[C:8]3[CH2:18][CH2:17][CH2:16][C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:9]=3[N:10]=[C:11]([NH2:13])[N:12]=2)[N:29]=1

Participants

3

Reactant 2

HCID 3457522-Chloro-4-aminopyrimidineHCID 86638144N4-(2-aminoethyl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine dihydrochloride

Product 1

HCID 44609411N4-{2-[(4-aminopyrimidin-2-yl)amino]ethyl}-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

Procedure

The product of Example 4B (67 mg, 0.196 mmol) and 6-amino-2-chloropyrimidine (33 mg, 0.254 mmol) were treated under the conditions of Example 1F to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.87 (d, J=5.55 Hz, 1H) 7.62-7.68 (m, 1H) 7.28-7.37 (m, 2H) 7.14-7.21 (m, 1H) 5.80 (d, J=5.55 Hz, 1H) 5.30-5.39 (m, 1H) 4.72 (s, 2H) 4.61 (s, 2H) 3.57-3.73 (m, 4H) 2.53 (t, J=6.94 Hz, 2H) 2.15 (t, J=6.35 Hz, 2H) 1.94-2.08 (m, 2H); MS (ESI+) m/z 363.0 (M+H)+.

Sources & evidence

ORD record
ord-ab108dec03ca40a39a46ac6fb0d0b0ab
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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