1-(Bromomethyl)-2,4-difluorobenzene → 5-[4-(2,4-Difluoro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamine

HRID 1015391Notes

Reaction equation

HRID 1015391 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.[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:21]=1[CH2:22]Br>>[F:19][C:20]1[CH:27]=[C:26]([F:28])[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 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 250045345-[4-(2,4-Difluoro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamineYield 88%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 2,4-Difluorobenzyl bromide (76.6 mg; 0.37 mmol) to obtain 65 mg. (88% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.95 (s, 1H), 8.87 (s, 1H), 7.67 (m, 3H), 7.48 (m, 1H), 7.24 (m, 3H), 7.09 (m, 1H), 3.61 (s, 2H), 3.02 (br d, J=10.8 Hz, 2H), 2.89 (m, 4H), 2.33 (m, 2H). ESIMS+371.5 m/z

Workup

  1. customto obtain 65 mg

Sources & evidence

ORD record
ord-4859d2fb3f114a769f315f008e315055
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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