Chloride → [3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochloride

HRID 2076038Notes

Reaction equation

HRID 2076038 reaction equation
C(OC([N:8]1[CH2:32][CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:11]2[N:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[CH:18]=3)[N:14]=[CH:15][C:10]=2[CH2:9]1)=O)(C)(C)C.[Cl-:39]>ClCCl.C(OCC)C>[ClH:39].[CH3:30][O:29][C:19]1[CH:18]=[C:17]([NH:16][C:13]2[N:14]=[CH:15][C:10]3[CH2:9][NH:8][CH2:32][CH:31]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:11]=3[N:12]=2)[CH:22]=[CH:21][C:20]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1

Participants

5

Reactant 2

HCID 312ChlorideHCID 441941562-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-8-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert.-butyl ester

Product 1

HCID 44194157[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(8-phenyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-8-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert.-butyl ester (75 mg, 0.15 mmol) in dichloromethane (1.5 mL) was added at 0° C. 2M hydrogene chloride (0.73 mL) in diethyl ether. The reaction was stirred at room temperature over night. The solvent was evaporated under reduced pressure to yield the title compound (70 mg, 100%) as a yellow solid. MS ISP (m/e): 413.4 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.01 (m, 2H), 9.23 (s, 1H), 8.57 (s, 1H), 7.71 (s, 1H), 7.59 (s, 1H), 7.26-7.38 (m, 6H), 7.15 (d, 1H), 4.56 (dd, 1H), 4.37 (m, 2H), 3.64 (m, 1H), 3.42 (m, 1H), 3.38 (s, 3H), 2.32 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b9fe06ce9e744f31a31a703190f8d252
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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