Hydrochloric Acid → HCID 59424565, compound

HRID 1711016Notes

Reaction equation

HRID 1711016 reaction equation
Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].Cl>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:21][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 98252-Fluoro-4-nitrophenolHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 59424565HCID 59424565, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 27 (0.400 g, 2.60 mmol) [G. B. Evans, R. H. Furneaux, et. al J. Org. Chem., 2001, 66, 17, 5723-5730] in diphenylether (25 ml) was added 2-fluoro-4-nitrophenol (614 mg, 3.90 mmol) and HCl (2N in Et2O) (0.19 ml, 3.90 mmol). The reaction mixture was heated at 120° C. for 4 hours, cooled to room temperature and concentrated under reduced pressure, to afford title compound 243 (610 mg, 86% yield) as a black solid. MS (m/z): 274.1 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-257c6a789b8440edaca1ed8874b946f9
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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