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

HRID 383257

反応式

HRID 383257 の反応式
[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

参加物

6

反応物 4

HCID 2723922Sodium ethoxide2 回HCID 3033972Mucobromic AcidHCID 5360545SodiumHCID 12301253Propionimidamide hydrochloride

生成物 1

HCID 669777025-Bromo-2-ethylpyrimidine-4-carboxylic acid収率 37%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒4 回

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d3a42bce36734cdfa320fdae2d93aa99
出典データセット
uspto-grants-2013_02
特許番号
US08367663B2

関連ノート

読み込み中…