Sodium Chloride → (6-Amino-5-ethynyl-pyridin-2-yl)-methanol

HRID 78173ノート

反応式

HRID 78173 の反応式
[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]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 592555002-Amino-6-hydroxymethyl-pyridine-3-carbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

生成物 1

HCID 55285940(6-Amino-5-ethynyl-pyridin-2-yl)-methanol収率 79.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  1. waitfor another 6 hours at room temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. concentrationwas concentrated under a reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-8332705e1d4a430bb2e1c0b6ead30dc1
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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