Dimethylamine → 2-Chloro-N,N-dimethylquinazolin-4-amine

HRID 1984863Notes

Reaction equation

HRID 1984863 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:13]([CH3:15])[CH3:14].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([N:13]([CH3:15])[CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2528862,4-DichloroquinazolineHCID 516892Sodium Bicarbonate

Product 1

HCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-dichloro-quinazoline (102 g, 530 mmol) in THF (1.2 L) was cooled to 4° C. and 50% aqueous Me2NH (139 mL, 1.33 mol) was added. The mixture was stirred at ambient temperature for 80 min. The solution was alkalized with saturated aqueous NaHCO3 (pH=9), and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, and concentrated. The residue was suspended in 50% Et2O in hexane (250 mL) and stirred at ambient temperature for 30 min. The solid was collected by filtration, washed with 50% Et2O in hexane, and dried at 80° C. to give (2-chloro-quinazolin-4-yl)-dimethyl-amine (104 g, 94%) as a pale yellow solid.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3 (three times)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. stirringstirred at ambient temperature for 30 min
  6. filtrationThe solid was collected by filtration
  7. washwashed with 50% Et2O in hexane
  8. customdried at 80° C.

Sources & evidence

ORD record
ord-49bfd9f20e484995800efc85c85d8252
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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