Dimethylformamide → HCID 59852844, compound

HRID 2373957Notes

Reaction equation

HRID 2373957 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[F:18])[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O.C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:2]2[N:7]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=3[F:18])[CH:5]=[CH:4][N:3]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 59853046HCID 59853046, compound

Product 1

HCID 59852844HCID 59852844, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-(2-fluoro-4-nitrophenoxy)pyrimidine (0.66 g, 2.44 mmol), 4-methoxybenzylamine (0.34 g, 3.45 mmol), K2CO3 (0.37 g, 2.66 mmol), and DMF (15 mL) was heated at 100° C. for 1 h. The mixture was cooled, diluted with H2O (100 mL) and extracted with EtOAc (100 mL). The organic phase was washed twice each with saturated NaHCO3 solution and brine. The organics were dried (MgSO4) and concentrated to give the crude product. Flash chromatography on SiO2 using 1-3% MeOH in CH2Cl2 as the eluent gave the title compound (275 mg, 29%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.40-8.21 (m, 2H), 8.16 (dd, 1H, J=8.8, 1.7 Hz), 7.98 (br s, 0.5H), 7.73-7.55 (m, 1.5H), 7.16 (br s, 1H), 6.85-6.71 (m, 3H), 6.37 (s, 1H), 4.43 (br s, 1H), 3.95 (br s, 1H), 3.69 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic phase was washed twice each with saturated NaHCO3 solution and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give the crude product

Sources & evidence

ORD record
ord-610d5e1b35fc4d62b9f408ee8b79466c
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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