Ethanol → HCID 86719385, compound

HRID 510340Notes

Reaction equation

HRID 510340 reaction equation
[Cl:1][C:2]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:4]=2[C:3]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1.[NH4+].[Cl-].O.CCO>C1COCC1.C(Cl)Cl.[Fe].CO>[NH2:25][C:21]1[CH:20]=[C:19]([N:18]2[C:5]3[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C:4]=3[C:3]([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[C:2]2[Cl:1])[CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 86719384HCID 86719384, compound

Product 1

HCID 86719385HCID 86719385, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 6-chloro-5-(4-chlorophenyl)-7-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylcarbamate (20) (1.3 g, 2.6 mmol), iron powder (2.9 g, 52.1 mmol) and NH4Cl (1.4 g, 26.0 mmol) in a mixture of THF (30 mL), H2O (15 mL) and EtOH (3 mL) was purged with N2 before heated to 50° C. for 8 hrs. The reaction was then cooled down to r.t. and was filtered through Celite pad. The filter cake was thoroughly washed with DCM. The filtrate was washed with H2O, brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatographic (silica gel, with 0 to 50% EA in a mixture of PE & DCM (1:1) and then 0 to 10% MeOH in DCM) to afford tert-butyl 7-(3-aminophenyl)-6-chloro-5-(4-chlorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylcarbamate (21) (421 mg, 35% yield) as a yellow solid. LC-MS (ESI): m/z (M/M+2) 468.6/470.6.

Workup

  1. customwas purged with N2
  2. temperatureThe reaction was then cooled down to r.t.
  3. filtrationwas filtered through Celite pad
  4. washThe filter cake was thoroughly washed with DCM
  5. washThe filtrate was washed with H2O, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatographic (silica gel
  9. additionwith 0 to 50% EA in a mixture of PE & DCM (1:1)

Sources & evidence

ORD record
ord-3e84cf38ae4d4957b6b3c154a90e7f54
Source dataset
uspto-grants-2015_08
Patent number
US09096604B2

Reaction notes

Loading…