Sodium Carbonate → HCID 59242025, compound

HRID 1876161Notes

Reaction equation

HRID 1876161 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=2)[N:3]=1.Cl.[CH3:24][NH2:25].C([O-])([O-])=O.[Na+].[Na+]>CC(O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH3:13])[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:22])[CH:8]=3)[N:3]=[C:2]([NH:25][CH3:24])[N:11]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6364545Methylamine hydrochlorideHCID 113928514-Quinazolinamine, 2-chloro-N-(4-methoxyphenyl)-N,6-dimethyl-

Product 1

HCID 59242025HCID 59242025, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (2-chloro-6-methyl-quinazolin-4-yl)-(4-methoxyphenyl)-methyl-amine (62.9 mg, 0.20 mmol), methylamine hydrochloride (145.8 mg, 2.2 mmol) and Na2CO3 (234.5 mg, 2.2 mmol) in i-PrOH (2 mL) was heated to 100° C. overnight. After cooling to room temperature the reaction mixture was concentrated onto SiO2 and purified by gradient MPLC (SiO2, 0 to 20% MeOH/CH2Cl2 with 0.1% NH4OH, 20 min). 20.3 mg (33%) of the title compound was obtained: 1H NMR (DMSO-d6, 90° C.) δ 7.93 (br s, 1 H), 7.38-7.52 (m, 2 H), 7.33 (d, 2 H), 7.08 (d, 2 H), 6.39 (s, 1 H), 3.83 (s, 3 H), 3.62 (s, 3 H), 3.06 (s, 3 H), 1.96 (s, 3 H). HRMS (ES) calcd for C18H21N4O [(M+H)] 309.1710, found 309.1714.

Workup

  1. concentrationwas concentrated onto SiO2
  2. custompurified by gradient MPLC (SiO2, 0 to 20% MeOH/CH2Cl2 with 0.1% NH4OH, 20 min)

Sources & evidence

ORD record
ord-30b0962b38c84831a7a52614e3e6092f
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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