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

HRID 1891884노트

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HRID 1891884 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a085d65b8ef944b8a08e7056057a18c4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507530B2

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