Potassium Carbonate → HCID 59242107, compound

HRID 1876146Notes

Reaction equation

HRID 1876146 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C.CCOC(C)=O>[CH3:32][O:31][C:29](=[O:30])[CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:9])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 114710894-(methyl(2-methylquinazolin-4-yl)amino)phenol

Product 1

HCID 59242107HCID 59242107, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(4-Hydroxy-phenyl)-(2-methyl-quinazolin-4-yl)-methyl-amine (468 mg, 1.41 mmol) and K2CO3 were dissolved in DMF (10 mL). Methyl bromoacetate (0.67 mL, 7.08 mmol) was added and the reaction was heated at 60° C. for 2 h. The mixture was cooled and diluted with EtOAc. The organics were washed with water (2×) and dried over MgSO4. The title compound was purified by preparative RPLC. 1H NMR (DMSO-d6) δ 7.64 (d, 1H), 7.59 (t, 1H), 7.20 (d, 2H), 7.05 (t, 1H), 7.0-6.9 (m, 3H), 4.85 (s, 2H), 3.71 (s, 3H), 3.50 (s, 3H), 2.58 (s, 3H); LC-MS (ESI+; 338 ([M+H]+)).

Workup

  1. temperatureThe mixture was cooled
  2. washThe organics were washed with water (2×)
  3. dry with materialdried over MgSO4
  4. customThe title compound was purified by preparative RPLC

Sources & evidence

ORD record
ord-b351d53ebbef4af691c4c848137e5e74
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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