Methanol → Methyl 5-aminopyrimidine-2-carboxylate

HRID 1526615

반응식

HRID 1526615 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15]O>C([O-])(O)=O.[Na+]>[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([O:10][CH3:15])=[O:9])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 122159975-Aminopyrimidine-2-carboxylic Acid

생성물 1

HCID 10654421Methyl 5-aminopyrimidine-2-carboxylate수율 68%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

A suspension of 5-aminopyrimidine-2-carboxylic acid (Goldenbridge Pharma, Inc.; 5.70 g, 41.0 mmol) in MeOH (120 mL) was cooled in an ice-water bath and treated dropwise with thionyl chloride (8.97 mL, 123 mmol). The resulting suspension was heated at reflux for 20 h and then concentrated to give a yellow solid. The solid was dissolved in saturated aqueous NaHCO3 (60 mL) and extracted into EtOAc using a Gregar Extractor. The extract was concentrated to give methyl 5-aminopyrimidine-2-carboxylate (4.26 g, 68% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 2H), 4.35 (br s, 2H), 4.02 (s, 3H).

후처리

  1. temperaturewas cooled in an ice-water bath
  2. temperatureThe resulting suspension was heated
  3. temperatureat reflux for 20 h
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. extractionextracted into EtOAc using a Gregar Extractor
  7. concentrationThe extract was concentrated

출처 및 근거

ORD 기록
ord-4fd510a635314d1b8ce240a831f8fb8d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

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