Hydrochloric Acid → 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3R)-tetrahydro-3-furanyl]oxy]-

HRID 1929243Notes

Reaction equation

HRID 1929243 reaction equation
CC(C)([O-])C.[K+].[OH:7][C@@H:8]1[CH2:12][CH2:11][O:10][CH2:9]1.[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28](F)=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20].Cl>CN(C)C=O.O>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:7][C@@H:8]4[CH2:12][CH2:11][O:10][CH2:9]4)=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 641512(-)-3-HydroxytetrahydrofuranHCID 10640649N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 669368164-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3R)-tetrahydro-3-furanyl]oxy]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

13.80 g of potassium tert-butoxide are added batchwise to a solution of 10.80 g of (R)-3-hydroxytetrahydrofuran in 100 ml of N,N-dimethylformamide while cooling with an ice bath. The reaction mixture is stirred for about one hour, then 10.40 g of 4-[(3-chloro-4-fluorophenyl)amino]-6-nitro-7-fluoroquinazoline are added batchwise. The cooling bath is then removed and the deep red reaction mixture is stirred for two hours at ambient temperature. For working up the reaction mixture is poured onto about 500 ml of water and neutralized with 2 N hydrochloric acid. The yellowish precipitate formed is suction filtered and dried at 70° C. in a circulating air drier. Yield: 12.80 g; melting point: 244° C.; mass spectrum (ESI−): m/z=403, 405 [M−H]−.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThe cooling bath is then removed
  3. customthe deep red reaction mixture
  4. stirringis stirred for two hours at ambient temperature
  5. customThe yellowish precipitate formed
  6. filtrationfiltered
  7. customdried at 70° C. in a circulating air drier

Sources & evidence

ORD record
ord-2c0b141a5a7040bd9181170a63d72633
Source dataset
uspto-grants-2012_05
Patent number
USRE043431E1

Reaction notes

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