Ammonia → 2-(p-Ethynylphenyl)-5-pentylpyrimidine

HRID 370680

反応式

HRID 370680 の反応式
N.[Na].Br[C:4](Br)=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:14][N:13]=2)=[CH:8][CH:7]=1>C(OCC)C.[N+]([O-])([O-])=O.[Fe+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[C:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:16][N:17]=2)=[CH:10][CH:11]=1)#[CH:4]

参加物

6

反応物 3

HCID 222AmmoniaHCID 5360545Sodium2 回HCID 202750122-[p-(2,2-Dibromovinyl)phenyl]-5-pentylpyrimidine

生成物 1

HCID 202749782-(p-Ethynylphenyl)-5-pentylpyrimidine収率 71.8%

試薬・触媒・溶媒 2

HCID 25251Ferric nitrate触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

About 100 ml of ammonia were condensed at -78° C. under argon gasification in a sulphonation flask equipped with a gas inlet tube, dry-ice condenser and mechanical stirrer and treated with sodium metal until the blue colouration persisted. A spatula tip of iron (III) nitrate was subsequently added, the now greyish mixture was treated portionwise with 820 mg of sodium metal and the resulting mixture was stirred at -78° C. for a further 30 minutes. A solution of 1.02 g of 2-[p-(2,2-dibromovinyl)phenyl]-5-pentylpyrimidine in 10 ml of diethyl ether was added dropwise within 5 minutes, then the green-yellow mixture was stirred at -78° C. for a further 45 minutes, the ammonia was evaporated and the mixture was subsequently treated with 30 ml of saturated ammonium chloride solution and extracted three times with 50 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of water each time and once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the resulting orange oil on silica gel with 10% ethyl acetate/petroleum ether gave 447 mg (71%) of 2-(p-ethynylphenyl)-5-pentylpyrimidine as colourless crystals; m.p. 72.3° C.

後処理

  1. customcondensed at -78° C. under argon gasification in a sulphonation flask
  2. customequipped with a gas inlet tube, dry-ice condenser and mechanical stirrer
  3. stirringthe green-yellow mixture was stirred at -78° C. for a further 45 minutes
  4. customthe ammonia was evaporated
  5. additionthe mixture was subsequently treated with 30 ml of saturated ammonium chloride solution
  6. extractionextracted three times with 50 ml of diethyl ether each time
  7. washThe organic phases were washed twice with 50 ml of water each time
  8. dry with materialonce with saturated sodium chloride solution, dried over magnesium sulphate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-61185f5df7bc452f83bff941e3f0521a
出典データセット
uspto-grants-1985_07
特許番号
US04528114

関連ノート

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