2-(Pyrimidin-4-yl)quinazoline-4-carboxylic acid → HCID 86270400, compound

HRID 717447Notes

Reaction equation

HRID 717447 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]([O:32][CH3:33])=[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]([O:32][CH3:33])[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 904111806-Methoxy-1,2,3,4-tetrahydroisoquinolin-5-ol hydrochloride

Product 1

HCID 86270400HCID 86270400, compoundYield 13%

Procedure

Reaction of 2-(4-pyrimidinyl)quinazoline-4-carboxylic acid with 5-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride gave compound 70 (13% yield) as a light brown solid. 1H NMR (300 MHz, DMSO-d6) δ 2.61 and 2.90 (2t, 2H), 3.49 and 4.04 (2t, 2H), 3.73 and 3.80 (2s, 3H), 4.38 and 4.92 (2s, 2H), 6.30 and 6.77 (2d, 1H), 6.70 and 6.91 (2d, 1H), 7.90-8.31 (m, 4H), 8.48-8.54 (m, 1H), 8.68-8.74 (2s, 1H), 9.06-9.43 (m, 1H), 9.44 (s, 1H); MS (ESI) m/z 414 ([M+H]+).

Sources & evidence

ORD record
ord-692e948582f3431f8916c5bcddc89aef
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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