2-(Pyrimidin-4-yl)quinazoline-4-carboxylic acid → HCID 86270026, compound

HRID 717449Notes

Reaction equation

HRID 717449 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:16]=[C:15]([C:17]([OH:19])=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[N:3][CH:2]=1.Cl.[OH:21][C:22]1[C:31]([CH3:32])=[CH:30][CH:29]=[C:28]2[C:23]=1[CH2:24][CH2:25][NH:26][CH2:27]2>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:16]=[C:15]([C:17]([N:26]3[CH2:25][CH2:24][C:23]4[C:28](=[CH:29][CH:30]=[C:31]([CH3:32])[C:22]=4[OH:21])[CH2:27]3)=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[N:3][CH:2]=1

Participants

3

Reactant 2

HCID 904109312-(Pyrimidin-4-yl)quinazoline-4-carboxylic acidHCID 904112275-Hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 86270026HCID 86270026, compoundYield 15%

Procedure

Reaction of 2-(4-pyrimidinyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 73 (15% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.25-2.28 (m, 3H), 2.78 and 3.05 (2t, 2H), 3.56 and 4.21 (2t, 2H), 4.46 and 5.09 (2s, 2H), 6.30-7.07 (m, 2H), 7.74-7.82 (m, 1H), 8.04-8.12 (m, 2H), 8.35-8.42 (m, 1H), 8.65-8.75 (m, 1H), 9.02-9.10 (m, 1H), 9.55-9.60 (m, 1H); MS (ESI) m/z 398 ([M+H]+).

Sources & evidence

ORD record
ord-efd99436380a4b31875b0405941f7b51
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

Loading…