Ethanol → HCID 178508576, compound

HRID 1492146Notes

Reaction equation

HRID 1492146 reaction equation
[F:1][C:2]1[C:3]([NH2:10])=[N:4][C:5]([NH2:9])=[N:6][C:7]=1Cl.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([OH:19])C>>[F:1][C:2]1[C:3]([NH2:10])=[N+:4]([O-:19])[C:5]([NH2:9])=[N:6][C:7]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 15221578HCID 15221578, compound

Product 1

HCID 178508576HCID 178508576, compound

Procedure

5-Fluoro-6-chloro-2,4-pyrimidinediamine, 3-oxide (6) (58 mg, 0.32 mmol), piperidine (112 mg, 1.3 mmol) and 95% ethanol (2.6 ml) were charged to a round bottom flask and refluxed for 2 days. The solution was concentrated and the residue was chromatographed on silica gel (elution with 15% methanol/chloroform+2% ammonium hydroxide), yielding 5fluoro-6-piperidinyl-2,4-pyrimidinediamine 3-oxide as a white solid. (51 mg, 69%): MS (70 eV, EI)m/z (relative intensity) 84 (100), 227 (M+, 98), 210 (55), 43 (30), 40 (24); 1H NMR (CD3OD)δ4.91 (s, 4H), 3.61 (mult., 4H), 1.67 (mult., 2H), 1.60 (mult., 4H); 13C NMR (CD3OD) ppm 150, 147.5, 147, 123, 49.86, 27.05, 25.82. Exact Mass Calcd for C9H4N5OF: 227.1182. Found: 227.1188. ##STR2##

Workup

  1. temperaturerefluxed for 2 days
  2. concentrationThe solution was concentrated
  3. customthe residue was chromatographed on silica gel (elution with 15% methanol/chloroform+2% ammonium hydroxide)

Sources & evidence

ORD record
ord-a99bd2d40ab64e82a9f14603f121c0ca
Source dataset
uspto-grants-1994_12
Patent number
US05373012

Reaction notes

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