Propargyl alcohol → HCID 22599874、化合物

HRID 1592081ノート

反応式

HRID 1592081 の反応式
[H-].[Na+].[CH2:3]([OH:6])[C:4]#[CH:5].Cl[C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=[CH:10][N:9]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:15]([O:14][C:12]1[CH:13]=[C:8]([O:6][CH2:3][C:4]#[CH:5])[N:9]=[CH:10][N:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225998714-(Benzyloxy)-6-chloropyrimidine

生成物 1

HCID 22599874HCID 22599874、化合物収率 39%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In 4 ml of tetrahydrofuran was suspended 0.13 g of sodium hydride (60% in oil), to which 0.7 ml of a tetrahydrofuran solution containing 0.12 g of 2-propyn-1-ol was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes and then cooled to 0° C., to which 0.7 ml of a tetrahydrofuran solution containing 0.4 g of 4-chloro-6-benzyloxypyrimidine was slowly added dropwise. The mixture was further stirred at 0° C. for 4.5 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.17 g of 4-benzyloxy-6-(2-propynyloxy)pyrimidine (the present compound (13)).

後処理

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 20 minutes
  3. additionwas slowly added dropwise
  4. stirringThe mixture was further stirred at 0° C. for 4.5 hours
  5. extractionextracted three times with chloroform
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-50e0c70df9ac45c6b6651131080f9a6e
出典データセット
uspto-grants-2007_11
特許番号
US07291730B2

反応ノート

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