tert-Butanol → HCID 69924378、化合物

HRID 1005988ノート

反応式

HRID 1005988 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:5](C(O)=O)=[CH:4][N:3]=1.C([N:21]([CH2:24]C)CC)C.[C:26]([OH:30])([CH3:29])([CH3:28])[CH3:27].C1C[O:34]CC1>>[C:26]([O:30][C:24](=[O:34])[NH:21][C:5]1[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:7][C:2]([CH3:1])=[N:3][CH:4]=1)([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 226742712-Methyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid

生成物 1

HCID 69924378HCID 69924378、化合物収率 56%

実験手順

To a solution of 2.50 g (10.24 mmol) 2-methyl-4-o-tolyloxy-pyrimidine-5-carboxylic acid, 1.43 ml triethylamine (10.24 mmol) and 1.9 ml (20.4 mmol) t-butanol in 50 ml THF, 2.2 ml (10.24 mmol) diphenylphosporylazide were added and the resulting solution heated at reflux for 12 hrs. After evaporation of the solvent, the residue was distributed between CH2Cl2 and H2O. The aquoeus phase was extracted twice with 80 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1) to give 1.83 g (56%) (2-methyl-4-o-tolyloxy-pyrimidin-5-yl)-carbamic acid tert.-butyl ester as a colorless solid, MS (ISP): 316.3 (M+H)+.

後処理

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 12 hrs
  3. customAfter evaporation of the solvent
  4. extractionThe aquoeus phase was extracted twice with 80 ml CH2Cl2
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1)

出典と根拠

ORDレコード
ord-9b01b11a6b904658af963ffc9c386803
出典データセット
uspto-grants-2004_09
特許番号
US06787539B2

反応ノート

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