Acetamidine monohydrochloride → 5-Bromo-2-methylpyrimidine-4-carboxylic acid

HRID 383256

반응식

HRID 383256 반응식
[Na].[O-]CC.[Na+].Cl.[C:7]([NH2:10])(=[NH:9])[CH3:8].[C:11]([OH:19])(=[O:18])/[C:12](=[C:14](\[CH:16]=O)/[Br:15])/Br>C(O)C>[Br:15][C:14]1[C:12]([C:11]([OH:19])=[O:18])=[N:9][C:7]([CH3:8])=[N:10][CH:16]=1

참가 물질

6

반응물 4

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide3회HCID 3033972Mucobromic AcidHCID 5360545Sodium

생성물 1

HCID 2562105-Bromo-2-methylpyrimidine-4-carboxylic acid수율 42%

시약·촉매·용매 1

HCID 702Ethanol용매5회

반응 조건

온도
50 °C

실험 절차

Sodium (356 mg, 15.5 mmol) was carefully added to ethanol (5.9 mL) to prepare sodium ethoxide solution in ethanol. The above freshly prepared sodium ethoxide in ethanol solution (3.5 mL) was added to a stirred suspension of acetamidine hydrochloride (0.91 g, 9.69 mmol). The mixture was warmed to 50° C., then the heating bath was removed and a solution of mucobromic acid (1 g, 3.87 mmol) in ethanol was added dropwise at a rate which maintained a constant temperature, followed by a further sodium ethoxide in ethanol solution (2 mL). After cooling, the mixture was filtered and evaporated to a residue which was shaken vigorously with hydrochloric acid (2 M×2.4 mL). The brown precipitate was filtered and washed with cold water, then freeze-dried to give 5-bromo-2-methylpyrimidine-4-carboxylic acid (350 mg, 42%) as a brown solid. LCMS: 218 [M+1]+, 1H NMR (400 MHz, DMSO-d6): δ 2.62 (s, 3H), 9.03 (s, 1H).

후처리

  1. customthe heating bath was removed
  2. temperaturemaintained a constant temperature
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customevaporated to a residue which
  6. filtrationThe brown precipitate was filtered
  7. washwashed with cold water
  8. customfreeze-dried

출처 및 근거

ORD 기록
ord-e704524bd7434e949b9ed94f908b0563
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367663B2

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