Sodium ethoxide → 5-Bromo-2-ethylpyrimidine-4-carboxylic acid

HRID 383257

반응식

HRID 383257 반응식
[Na].[O-]CC.[Na+].Cl.[C:7](=[NH:11])([NH2:10])[CH2:8][CH3:9].[C:12]([OH:20])(=[O:19])/[C:13](=[C:15](\[CH:17]=O)/[Br:16])/Br>C(O)C>[Br:16][C:15]1[C:13]([C:12]([OH:20])=[O:19])=[N:11][C:7]([CH2:8][CH3:9])=[N:10][CH:17]=1

참가 물질

6

반응물 4

HCID 2723922Sodium ethoxide2회HCID 3033972Mucobromic AcidHCID 5360545SodiumHCID 12301253Propionimidamide hydrochloride

생성물 1

HCID 669777025-Bromo-2-ethylpyrimidine-4-carboxylic acid수율 37%

시약·촉매·용매 1

HCID 702Ethanol용매4회

반응 조건

온도
55 °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 ethanol solution (3.5 mL) was added to a stirred suspension of propionimidamide hydrochloride (1.05 g, 9.69 mmol). The mixture was warmed to 55° 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 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 off and washed with cold water, then freeze-dried to give 5-Bromo-2-ethylpyrimidine-4-carboxylic acid (330 mg, 37%) as a yellow solid. LCMS: 231 [M+1]+, 1H NMR (400 MHz, DMSO-d6): δ 1.25 (t, J=7.6 Hz, 3H), 2.88 (q, J=7.6 Hz, 2H), 9.05 (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 off
  7. washwashed with cold water
  8. customfreeze-dried

출처 및 근거

ORD 기록
ord-d3a42bce36734cdfa320fdae2d93aa99
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367663B2

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