Methylamine → 2-chloro-N-methylquinazolin-4-amine

HRID 1984901Notes

Reaction equation

HRID 1984901 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.[CH3:13][NH2:14].C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([NH:14][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2528862,4-DichloroquinazolineHCID 516892Sodium Bicarbonate

Product 1

HCID 3180572-chloro-N-methylquinazolin-4-amineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-dichloro-quinazoline obtained in step A of example 1 (125 g, 628 mmol) in THF (1 L) was cooled to 4° C. and 40% aqueous MeNH2 (136 mL, 1.57 mol) was added. The mixture was stirred at ambient temperature for 80 min. The solution was alkalized with saturated aqueous NaHCO3 (pH=9) and concentrated. The precipitate was collected by filtration, washed with H2O and hexane, and dried at 80° C. to give (2-chloro-quinazolin-4-yl)-methyl-amine (114 g, 94%) as a white solid.

Workup

  1. concentrationconcentrated
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O and hexane
  4. customdried at 80° C.

Sources & evidence

ORD record
ord-8f0f04c76c0b4376a543919d9f1881a3
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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