N-BOC-ethylenediamine → tert-butyl 2-[(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)amino]ethylcarbamate

HRID 2386983Notes

Reaction equation

HRID 2386983 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].Cl[C:13]1[C:14]2[CH2:24][CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:15]=2[N:16]=[C:17]([NH2:19])[N:18]=1>>[NH2:19][C:17]1[N:18]=[C:13]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[C:14]2[CH2:24][CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[C:15]=2[N:16]=1

Participants

3

Reactant 2

HCID 187201N-BOC-ethylenediamineHCID 866218984-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

Product 1

HCID 68604420tert-butyl 2-[(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)amino]ethylcarbamate

Procedure

tert-Butyl 2-aminoethylcarbamate (595 mg, 3.71 mmol) and the product from Example 1C (702 mg, 2.86 mmol) were treated under the conditions described in Example 1D to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.38 (s, 9H) 1.97-2.08 (m, 2H) 2.15 (t, J=6.27 Hz, 2H) 2.43-2.49 (m, 2H) 3.15 (q, J=6.22 Hz, 2H) 3.33-3.42 (m, 2H) 5.84 (s, 2H) 6.68 (s, 1H) 6.89 (t, J=5.43 Hz, 1H) 7.20-7.27 (m, 1H) 7.27-7.37 (m, 2H) 7.49-7.57 (m, 1H); MS (ESI+) m/z 370.0 (M+H)+.

Sources & evidence

ORD record
ord-b991810c81b445a6b6e43d30ab71c677
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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