tert-Butyl piperazine-1-carboxylate → 8-Phenyl-4-(piperazin-1-yl)-5,6,7,8-tetrahydroquinazolin-2-amine

Reaction equation

CC1C=CC(S(O[C:12]2[C:13]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]([CH3:25])([CH3:24])[C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)(=O)=O)=CC=1.[N:26]1(C(OC(C)(C)C)=O)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.N1C[CH2:42][C@@H:41](NC(=O)OC(C)(C)C)[CH2:40]1>>[C:19]1([CH:20]2[C:12]3[N:17]=[C:16]([NH2:18])[N:15]=[C:14]([N:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[C:13]=3[CH2:23][CH2:22][CH2:21]2)[CH:24]=[CH:42][CH:41]=[CH:40][CH:25]=1

Participants

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylate

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

HCID 866348802-amino-9,9-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 444668728-Phenyl-4-(piperazin-1-yl)-5,6,7,8-tetrahydroquinazolin-2-amine

Procedure

The title compound was prepared according to the procedures of Examples 1E and 1F, substituting the product from Example 9C for the product from Example 1D and substituting tert-butyl piperazine-1-carboxylate for (R)-tert-butyl pyrrolidin-3-ylcarbamate. 1H NMR (300 MHz, CDCl3) δ 7.24 (m, 2H), 7.18 (m, J=7.54 Hz, 1H), 7.06 (d, J=8.33 Hz, 1H), 4.55 (s, 2H), 3.99 (t, J=6.94 Hz, 1H), 3.31 (m, 4H), 2.98 (m, 4H), 2.55 (m, 2H), 2.20 (m, 1H), 1.79 (m, 3H); MS (ESI+) m/z 310 (M+H)+.