1,1'-Carbonyldiimidazole → tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperazine-1-carboxylate

HRID 1520114Notes

Reaction equation

HRID 1520114 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.NC1C=C([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)C=CC=1CN.C1N=CN(C(N2C=NC=C2)=O)C=1>>[O:12]=[C:8]1[NH:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([N:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:27]3)=[CH:3][CH:4]=2)[NH:9]1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 468564837-Bromo-3,4-dihydro-2(1H)-quinazolinoneHCID 131732196tert-Butyl 4-(3-amino-4-(aminomethyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 117796384tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperazine-1-carboxylateYield 75%

Procedure

Following the same procedure adopted for the synthesis of compound 13, reaction of compound 20 with CDI afforded 0.73 g (75%) of compound 16 as an off-white solid, m.p. 218-219° C.; IR (KBr) νmax. cm−1: 3211, 3166 (NH), 3037 (Ar—H), 1693 (C═O), 1610, 1519, 1417 (C═C). 1H NMR (500 MHz, CDCl3) S=1.48 (s, 9H, (CH3)3C); 3.00 (m, 4H, 2CH2); 3.56 (m, 4H, 2CH2); 4.48 (s, 2H, CH2); 6.62 (d, 1H, J=2.5 Hz, H-8); 6.64 (d, 1H, J=8.5 Hz, H-5); 6.74 (dd, 1H, J=2.5, 8.4 Hz, H-6); 7.80 (br.s, 1H, NH); 13C NMR (125.7 MHz, CDCl3) δ=28.65 (CH3)3C), 43.31 (CH2), 43.98 (CH2), 50.63 (CH2), 80.18 (CH3)3C), 115.13 (C-8/C-6), 115.21 (C-8/C-6), 117.59 (C-5), 118.35 (C-5), 130.66 (C-5), 147.20 (C-5), 154.91 (C═O), 155.95 (C═O). Calculated (%) for C17H24N4O3 (332.18); C: 61.43, H: 7.28, N: 16.86. found (%) C: 61.37, H: 7.32, N: 16.80.

Sources & evidence

ORD record
ord-711ce5e5c5814147bc2b4482cfa17810
Source dataset
uspto-grants-2015_07
Patent number
US09073900B2

Reaction notes

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