Sodium Bicarbonate → HCID 68849783, compound

HRID 1984916Notes

Reaction equation

HRID 1984916 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([N:22]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>C(O)CCC>[CH2:15]([N:22]1[CH2:26][CH2:25][CH:24]([NH:27][C:2]2[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27566131-Benzyl-3-aminopyrrolidineHCID 126843422-Chloro-N,N-dimethylquinazolin-4-amine

Product 1

HCID 68849783HCID 68849783, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (5.1 g, 28.9 mmol) and 1-Benzyl-pyrrolidin-3-ylamine (5.1 g, 28.9 mmol) in BuOH (8 mL) was stirred at reflux for 26 hr, poured into saturated aqueous NaHCO3, and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography (NH-silica gel, 10% to 16% EtOAc in hexane) to give N2-(1-benzyl-pyrrolidin-3-yl)-N4,N4-dimethyl-quinazoline-2,4-diamine (3.37 g, 50%) as a pale yellow solid.

Workup

  1. temperatureat reflux for 26 hr
  2. extractionthe aqueous layer was extracted with CHCl3 (three times)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (NH-silica gel, 10% to 16% EtOAc in hexane)

Sources & evidence

ORD record
ord-6c96ca883de7421d8aea9c82ae749a35
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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