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Diethyl Ether → 2-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Butyl Ester

HRID 1039370
Notes
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Reaction equation

HRID 1039370 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:31])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][OH:18])[N:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[C:9]2=[O:30])=[O:5])[CH3:2].[CH2:32](OC(C1C(C)=C2C(=CC=1C)N=C(COCC1C=CC=CC=1)N(C1C=CC=CC=1S(=O)(=O)NC)C2=O)=O)[CH3:33].C(OCC)C>C1COCC1.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:31])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][OH:18])[N:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25](=[O:29])(=[O:28])[NH:26][CH3:27])[C:9]2=[O:30])=[O:5])[CH2:2][CH2:32][CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 114763142-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl esterHCID 66815225HCID 66815225, compound

Product 1

HCID 115980582-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Butyl Ester

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

Preparation of 2-Hydroxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl ester: A solution of 2-Benzyloxymethyl-5,7-dimethyl-3-(2-methylsulfamoyl-phenyl)-4-oxo-3,4-dihydro-quinazoline-6-carboxylic acid ethyl ester (15 g, 0.028 mol) in anhydrous THF (270 mL) is degassed under house vacuum. Palladium on activated charcoal (Acros, 10% Pd, 930 mg) is added and the suspension is flushed with hydrogen (balloon). The suspension is stirred under hydrogen overnight. TLC and LCMS analysis indicates that starting material remained. The reaction mixture is filtered through Celite, and the catalyst is washed sequentially with methanol, DCM and methanol. The filtrate is evaporated to give a cream solid. Trituration with diethyl ether provides a white solid which is removed by filtration and dried under high vacuum to provide the title compound. The ethereal filtrate, which contains un-reacted starting material, is evaporated in vacuo and the residue is subjected to a second cycle of hydrogenation (Pd—C, 920 mg): after stirring overnight under hydrogen TLC/LCMS indicated absence of starting material. The reaction mixture is worked-up as above to provide the title compound as a white solid.

Workup

  1. customthe suspension is flushed with hydrogen (balloon)
  2. filtrationThe reaction mixture is filtered through Celite
  3. washthe catalyst is washed sequentially with methanol, DCM and methanol
  4. customThe filtrate is evaporated
  5. customto give a cream solid
  6. customis removed by filtration
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-09e67b9cdd4b4028864f23a08f79f3eb
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552015B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes