o-Xylyl bromide → 5-[1-(2-Methylbenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine

HRID 1015332Notes

Reaction equation

C(N)C1C=CC=CC=1.[NH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]3)[CH2:11][CH2:10]1.[CH3:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>>[CH3:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[C:19]([NH2:28])=[N:20][C:21]([NH2:27])=[N:22]3)[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 6992o-Xylyl bromide

HCID 7504Benzylamine

HCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 250074325-[1-(2-Methylbenzyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamineYield 89%

Procedure

The benzylamine was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (75 mg; 0.27 mmol) and 2-methylbenzyl bromide (65 mg; 0.35 mmol) via Method BB to yield 91 mg. (89% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.34 (t, J=8.0 Hz, 1H), 7.21 (m, 3H), 7.14 (m, 3H), 6.76 (d, J=8.0 Hz, 1H), 6.52 (d, J=8.4, 11H), 5.94 (br s, 2H), 3.98 (d, J=6.4 Hz, 2H), 3.41 (s, 3H), 2.83 (br, d, J=11.6 Hz, 2H), 2.32 (s, 3H), 2.00 (t, J=10.4 Hz, 2H), 1.9 (m, 1H), 1.73 (d, J=12.8 Hz, 2H), 1.31 (m, 2H). MS m/z (ESI) 378 (M+H)+.

Workup

customto yield 91 mg

Sources & evidence

ORD record: ord-81168662ca804d8d8af55e487349895d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985755B2

Reaction notes

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