Ammonium fluoride → HCID 59242038, compound

HRID 1876157Notes

Reaction equation

HRID 1876157 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH4+].[F-:23]>CN1CCCC1=O.C(Cl)Cl>[F:23][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 25516Ammonium fluorideHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 59242038HCID 59242038, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine 0.150 g (0.5 mmol) and NH4F 0.5 g in 1-methyl-2-pyrrolidinone 3 mL was stirred at 120° C. for 16 h. The reaction mixture was diluted with CH2Cl2 10 mL and directly subjected to gradient column chromatography (EtOAc/hexanes, 0% to 100%) to give the crude titled compound product in 10% yield, which was further purified with preparative HPLC. 1H NMR (CD3OD, 400 MHz): δ 7.48-7.43 (m, 1H), 7.25-7.19 (m, 3H), 7.02 (d, 2H, J=9.0 Hz), 6.82-6.73 (m, 2H), 3.84 (s, 3H), 3.58 (s, 3H). 19F NMR (CD3OD):−77 (s). m/e: 284.1 (M+1).

Sources & evidence

ORD record
ord-8fd51fc652d3494fb140855eed34a810
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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