Water → 2-Chloro-6-(2,4-difluoro-phenoxy)-quinazoline

HRID 1292863

Reaction equation

HRID 1292863 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[CH:8]=2)[N:3]=1.NC(CC)(CO)CO.O>CN1C(=O)CCC1>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 82822-Amino-2-ethyl-1,3-propanediolHCID 589051302-Chloro-6-(2,4-difluoro-phenoxy)-quinazolin-4-ylamine

Product 1

HCID 589051372-Chloro-6-(2,4-difluoro-phenoxy)-quinazolineYield 60.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound (1G) (250 mg, 0.85 mmol) and 2-amino-2-ethyl-1,3-propanediol (298 mg, 2.5 mmol) in NMP (0.25 mL) were stirred at 120° C. for 4 h. After cooling to room temperature, the reaction mixture was poured into water and extracted with EtOAc (2×25 mL). The combined organic layers were dried over sodium sulfate and evaporated in vacuo. The crude product was purified by chromatography (silica gel, CH2Cl2: MeOH, 95:5) to afford 150 mg of the above-titled compound (Example 1). Mp=110-112.9° C. MW (M+H)+=376.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe crude product was purified by chromatography (silica gel, CH2Cl2: MeOH, 95:5)

Sources & evidence

ORD record
ord-2babf05be6bd4834bda86386d146613a
Source dataset
uspto-grants-2007_07
Patent number
US07238698B2

Linked notes

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