Tetrahydrofuran → 4-Quinazolinamine, 2-chloro-6,7-dimethoxy-N-methyl-

HRID 1156018Notes

Reaction equation

HRID 1156018 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.O1CCC[CH2:18]1>CN>[Cl:1][C:2]1[N:11]=[C:10]([NH:12][CH3:18])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamine

Product 1

HCID 130363934-Quinazolinamine, 2-chloro-6,7-dimethoxy-N-methyl-

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

To a solution of 2-chloro-4-amino-6,7-dimethoxyquinazoline (2.0 g) in tetrahydrofuran (100 ml), methylamine was introduced over a period of 15 min. The reaction mixture was stirred for 2 hr at room temperature and evaporated. The residue was triturated with cold aqueous sodium carbonate solution and the solid was washed and dried to give 1.769 g of 2-chloro-4-methylamino-6,7-dimethoxyquinazoline. A portion of this compound was crystallized from methylene chloride-hexane to mp 216°-217° C.; ir (nujol mull) 3470 cm-1 ; nmr (DMSO-d6) δ 3.0 (d, 3H), 3.9 (s, 6H), 7.05 (s, 1H), 7.55 (s, 1H) and 8.3 (broad s, 1H); and Anal. Calcd for C11H12ClN3O2 : C, 52.07% H, 4.77% N, 16.56% and Found: C, 51.95% H, 4.70% N, 16.45%.

Workup

  1. customevaporated
  2. customThe residue was triturated with cold aqueous sodium carbonate solution
  3. washthe solid was washed
  4. customdried

Sources & evidence

ORD record
ord-83167b4cd65c41359b7176e7545447bf
Source dataset
uspto-grants-1982_06
Patent number
US04333937

Reaction notes

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