3-Methyl-2-butanol → 4-(2-Butynyloxy)-5-chloro-6-(1,2-dimethylpropyloxy)pyrimidine

HRID 1354127

反応式

HRID 1354127 の反応式
[H-].[Na+].[CH3:3][CH:4]([CH3:8])[CH:5]([OH:7])[CH3:6].Cl[C:10]1[C:15]([Cl:16])=[C:14](Cl)[N:13]=[CH:12][N:11]=1.[CH2:18]([OH:22])[C:19]#[C:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH2:18]([O:22][C:10]1[C:15]([Cl:16])=[C:14]([O:7][CH:5]([CH3:6])[CH:4]([CH3:8])[CH3:3])[N:13]=[CH:12][N:11]=1)[C:19]#[C:20][CH3:21]

参加物

7

反応物 5

HCID 117323-Methyl-2-butanolHCID 129912-Butyn-1-olHCID 24758Sodium hydride2 回HCID 25517Ammonium ChlorideHCID 2490074,5,6-Trichloropyrimidine

生成物 1

HCID 211044134-(2-Butynyloxy)-5-chloro-6-(1,2-dimethylpropyloxy)pyrimidine収率 51.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In 2 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.3 ml of a solution containing 0.10 g of 3-methyl-2-butanol was added dropwise at 0° C., followed by stirring for 10 minutes. To this was added dropwise 0.3 ml of a solution containing 0.20 g of 4,5,6-trichloropyrimidine in tetrahydrofuran, followed by stirring at the same temperature for 6 hours. To this was added dropwise 0.3 ml of a solution containing 0.08 g of 2-butyn-1-ol in tetrahydrofuran and further added 0.05 g of sodium hydride (60% in oil), followed by stirring at room temperature for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.15 g of 4-(2-butynyloxy)-5-chloro-6-(1,2-dimethylpropyloxy)pyrimidine (the present compound (24)).

後処理

  1. additionwas added dropwise at 0° C.
  2. stirringby stirring at the same temperature for 6 hours
  3. stirringby stirring at room temperature for 3 hours
  4. extractionwas extracted three times with t-butyl methyl ether
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-620125e0319045c89786a190eb53a5fb
出典データセット
uspto-grants-2007_05
特許番号
US07223769B2

関連ノート

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