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

HRID 383256

反応式

HRID 383256 の反応式
[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

参加物

6

反応物 4

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxide3 回HCID 3033972Mucobromic AcidHCID 5360545Sodium

生成物 1

HCID 2562105-Bromo-2-methylpyrimidine-4-carboxylic acid収率 42%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒5 回

反応条件

温度
50 °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 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).

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
  7. washwashed with cold water
  8. customfreeze-dried

出典と根拠

ORDレコード
ord-e704524bd7434e949b9ed94f908b0563
出典データセット
uspto-grants-2013_02
特許番号
US08367663B2

関連ノート

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