alpha-Bromo-o-chlorotoluene → 5-[4-(2-Chloro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamine

HRID 1015385Notes

Reaction equation

HRID 1015385 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Br>>[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 11905alpha-Bromo-o-chlorotolueneHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 250041935-[4-(2-Chloro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamineYield 63%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 2-Chlorobenzyl bromide (76 mg; 0.37 mmol) to obtain 46.6 mg. (63% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.4 (s, 1H), 10.1 (s, 1H), 9.0 (s, 1H), 7.72 (t, J=8.0 Hz, 2H), 7.52 (m, 1H), 7.45 (m, 1H), 7.34 (m, 3H), 7.22 (d, J=8.0 Hz, 1H), 3.68 (s, 2H), 3.03 (br d, J=10.8 Hz, 2H), 2.93 (m, 4H), 2.41 (m, 2H).

Workup

  1. customto obtain 46.6 mg

Sources & evidence

ORD record
ord-b681c591e14a4115aa4fb24d9fd5eff1
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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