Acetic Acid → 4-amino-6-chloro-pyrimidine-5-carbaldehyde O-methyl-oxime

HRID 907433Notes

Reaction equation

HRID 907433 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.Cl.[CH3:12][O:13][NH2:14].C(O)(=O)C>O>[CH3:12][O:13][N:14]=[CH:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[N:5][C:6]=1[Cl:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-HCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 724866374-amino-6-chloro-pyrimidine-5-carbaldehyde O-methyl-oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-amino-6-chloro-pyrimidine-5-carbaldehyde Compound 1a (1.0 g), O-methyl-hydroxylamine hydrochloride (0.94 g) and a mixed solvent of acetic acid (25 mL) and H2O (4 mL) were added to a flask. The mixture was stirred at rt overnight, then concentrated. The residue was suspended in H2O and extracted with EtOAc. The organic layer was separated, dried with MgSO4, then concentrated to afford 4-amino-6-chloro-pyrimidine-5-carbaldehyde O-methyl-oxime Compound 9a (0.97 g, 92%). 1H NMR (300 MHz, DMSO-d6) δ 8.55 (s, 1H), 8.50 (s, 1H), 8.25 (s, 1H), 7.70 (s, 1H), 3.98 (s, 3H). MS (ESI) m/z: 188 (M+H+).

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-73edc843b26a4234813eba600603c9fc
Source dataset
uspto-grants-2011_09
Patent number
US08013153B2

Reaction notes

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