3-Chloro-4-fluoroaniline → N-(3-Chloro-4-fluorophenyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 397401

Reaction equation

HRID 397401 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH3:11])[C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:14]=[C:15]([NH2:20])[CH:16]=[CH:17][C:18]=1[F:19]>CN(C=O)C.C(OCC)(=O)C.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:2]2[C:3]3[CH:10]=[CH:9][N:8]([CH3:11])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

6

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 2658294-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 22390983N-(3-Chloro-4-fluorophenyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 83%

Reagents, catalysts & solvents 3

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (398.8 mg, 2.4 mmol) and 3-chloro-4-fluoro-phenylamine (378 mg, 2.6 mmol) in DMF (6 mL) was stirred at room temperature for 2 minutes. To it was added silver triflate (672 mg, 2.6 mmol), the mixture was then stirred at 90° C. for 2 hours. The reaction was then diluted with ethyl acetate and filtered off the precipitate, washing the precipitate with 10% ammonia solution. The filtrate was extracted with ethyl acetate, dried and concentrated. The residue was triturated with ethyl acetate and filtered to give 549.1 mg (83%) of (3-chloro-4-fluoro-phenyl)-(7-methyl-7H-pyrrolo(2,3-d]pyrimidin-4-yl)-amine as an off-white solid. 1H NMR (300 MHz, DMSO-d6) 9.48 (s, 1H, NH), 8.35 (s, 1H), 8.29 (dd, J=2.7 & 6.8Hz, 1H), 7.75-7.80 (m, 1H), 7.37 (t, J=9.3 Hz, 1H), 7.30 (d, J=3.1 Hz, 1H), 6.77 (d, J=3.1 Hz, 1H), 3.75. (s, 3H, CH3). MS 277 [M++1].

Workup

  1. stirringthe mixture was then stirred at 90° C. for 2 hours
  2. filtrationfiltered off the precipitate
  3. washwashing the precipitate with 10% ammonia solution
  4. extractionThe filtrate was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was triturated with ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-4989893622504375a0c8d548ed83eb5d
Source dataset
uspto-grants-2003_08
Patent number
US06610688B2

Linked notes

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