Sodium Bicarbonate → HCID 18516898, compound

HRID 1370086Notes

Reaction equation

HRID 1370086 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:18]=[CH:19][C:20]([NH:23]CC3C=CC(OC)=CC=3)=[N:21][CH:22]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:7][CH:8]=1)#[N:2].C([O-])(O)=O.[Na+]>C(#N)C.CO.ClCCl.O>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[N:5]=2)=[CH:22][N:21]=1

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 18516931HCID 18516931, compound

Product 1

HCID 18516898HCID 18516898, compoundYield 57.1%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-cyano-N-(4-fluorophenyl)-4-[2-(4-methoxy-benzylamino)pyridin-5-yl]pyrimidine-2-amine (104 mg, 0.24 mmol) in acetonitrile (4 mL), MeOH (2 mL) and dichloromethane (2 mL), was added dropwise a solution of ceric ammonium nitrate (133 mg, 0.24 mmol) in water (1 mL). After 0.5 h the reaction was poured into saturated NaHCO3 and extracted with CHCl2. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the title compound (42 mg) as a buff solid, m.p. 289°. δH (d6 DMSO) 9.93 (1H, s), 8.76 (1H, d, J 2.3 Hz), 8.74 (1H, s), 8.09 (1H, dd, J 8.8, 2.5 Hz), 7.77-7.73 (2H, bm), 7.18-7.13 (2H, m), 6.85 (1H, s) and 6.63 (1H, d, J 8.8 Hz).

Workup

  1. extractionextracted with CHCl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2a3074e078614bdea89eaa270c1bca0a
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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