Sodium Chloride → (6-Amino-5-ethynyl-pyridin-2-yl)-methanol
Reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[C:4]([CH2:10][OH:11])[N:3]=1.[N+](=[C:14](P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+].[Cl-].[Na+]>CO>[NH2:1][C:2]1[N:3]=[C:4]([CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[C:8]#[CH:14]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 2-amino-6-hydroxymethyl-pyridine-3-carbaldehyde (16 mg, 0.11 mmol) described in Manufacturing Example 169-1-1 and methanol (1.5 mL) were added dimethyl (1-diazo-2-oxopropyl)phosphonate (30 mg, 0.16 mmol) and potassium carbonate (23 mg, 0.17 mmol) at −10° C., which was stirred for 10 minutes at 0° C., and then for another 6 hours at room temperature. A saturated ammonium chloride aqueous solution and saturated aqueous sodium chloride were added to the reaction mixture at the same temperature, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue thus obtained was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (13 mg, 47%, purity: 57%).
Workup
- waitfor another 6 hours at room temperature
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium chloride
- concentrationwas concentrated under a reduced pressure
- customThe residue thus obtained
- customwas purified by silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-736f35399d2e45b9a88e59591f211e4e
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153662B2
Reaction notes
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