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

HRID 2386980Notes

Reaction equation

HRID 2386980 reaction equation
Cl.Cl.[CH3:3][NH:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH2:14])[N:9]=1.Cl[C:16]1[C:17]2[CH2:27][CH2:26][CH2:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[C:18]=2[N:19]=[C:20]([NH2:22])[N:21]=1>>[NH2:14][C:10]1[N:9]=[C:8]([NH:7][CH2:6][CH2:5][N:4]([CH3:3])[C:16]2[C:17]3[CH2:27][CH2:26][CH2:25][C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[C:18]=3[N:19]=[C:20]([NH2:22])[N:21]=2)[CH:13]=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 866218984-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amineHCID 86638142N4-[2-(methylamino)ethyl]pyrimidine-2,4-diamine dihydrochloride

Product 1

HCID 44609409N4-{2-[(2-aminopyrimidin-4-yl)amino]ethyl}-N4-methyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidine-2,4-diamine

Procedure

The product from Example 2A (95 mg, 0.237 mmol) and the product from Example 1C (50 mg, 0.203 mmol) were combined under the conditions described in Example 1F to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.62-7.67 (m, 1H) 7.58 (d, J=5.43 Hz, 1H) 7.28-7.37 (m, 2H) 7.23-7.28 (m, 1H) 6.89 (s, 1H) 5.94 (s, 2H) 5.82 (s, 2H) 5.70 (d, J=5.76 Hz, 1H) 3.43-3.55 (m, 4H) 2.99-3.04 (m, 3H) 2.50-2.58 (m, 2H) 2.15 (dd, J=16.11, 5.93 Hz, 4H); MS (ESI+) m/z 377.0 (M+H)+.

Sources & evidence

ORD record
ord-aa0cabb7499d4561af5addb69a764f88
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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