HCID 68849783, compound → HCID 86610872, compound

HRID 1984917Notes

Reaction equation

HRID 1984917 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:23]=[C:22]([N:24]([CH3:26])[CH3:25])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:25][N:24]([CH3:26])[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([NH:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[N:23]=1

Participants

4

Reactant 1

HCID 68849783HCID 68849783, compound

Product 1

HCID 86610872HCID 86610872, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N2-(1-benzyl-pyrrolidin-3-yl)-N4,N4-dimethyl-quinazoline-2,4-diamine (3.3 g, 9.5 mmol) in MeOH (33 mL) was added Pd(OH)2 (660 mg). The mixture was stirred at ambient temperature under hydrogen atmosphere for 13 hr, and stirred at 50° C. for 6 hr. The mixture was filtered, concentrated, and purified by medium-pressure liquid chromatography (NH-silica gel, 1% to 3% MeOH in CHCl3) to give N4,N4-dimethyl-N2-pyrrolidin-3-yl-quinazoline-2,4-diamine (2.3 g, 93%) as a yellow oil.

Workup

  1. stirringstirred at 50° C. for 6 hr
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. custompurified by medium-pressure liquid chromatography (NH-silica gel, 1% to 3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-965a60ab26e84ae6877276d51c0b2776
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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