Carbon Dioxide → 2-Phenylamino-4-fluoromethyl-6-cyclopropylpyrimidine

HRID 358803ノート

反応式

HRID 358803 の反応式
C(N(S(F)(F)[F:7])CC)C.[C:10]1([NH:16][C:17]2[N:22]=[C:21]([CH2:23]O)[CH:20]=[C:19]([CH:25]3[CH2:27][CH2:26]3)[N:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+].C(=O)=O>ClCCl>[C:10]1([NH:16][C:17]2[N:22]=[C:21]([CH2:23][F:7])[CH:20]=[C:19]([CH:25]3[CH2:27][CH2:26]3)[N:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 198740942-Anilino-4-hydroxymethyl-6-cyclopropylpyrimidine

生成物 1

HCID 198740872-Phenylamino-4-fluoromethyl-6-cyclopropylpyrimidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

6.1 g (37.8 mmol) of diethylaminosulfur trifluoride in 15 ml of dichloromethane are slowly added dropwise within a period of one hour, with stirring, to a suspension of 9.1 g (37.8 mmol) of 2-phenylamino-4-hydroxymethyl-6-cyclopropylpyrimidine in 80 ml of dichloromethane. After the addition of 50 ml of ice-water, 50 ml of 10% aqueous sodium hydrogen carbonate solution are added dropwise. When the evolution of carbon dioxide has ceased, the organic phase is separated off and the aqueous phase is extracted twice with 20 ml of dichloromethane each time. The combined dichloromethane solutions are washed with 15 ml of water, dried over sodium sulfate and filtered, and the solvent is evaporated. The black oil which remains is purified by column chromatography over silica gel (toluene/chloroform/diethyl ether/petroleum ether (b.p. 50°-70° ); 5/3/1/1). After the eluant mixture has been evaporated off, the yellow oil is diluted with 20 ml of petroleum ether (b.p. 50°-70° C.) and crystallised at reduced temperature. The yellowish crystals melt at 50°-52° C. Yield: 4.9 g (20.1 mmol; 53% of the theoretical yield).

後処理

  1. additionare added dropwise
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted twice with 20 ml of dichloromethane each time
  4. washThe combined dichloromethane solutions are washed with 15 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customThe black oil which remains is purified by column chromatography over silica gel (toluene/chloroform/diethyl ether/petroleum ether (b.p. 50°-70° ); 5/3/1/1)
  9. customAfter the eluant mixture has been evaporated off
  10. additionthe yellow oil is diluted with 20 ml of petroleum ether (b.p. 50°-70° C.)
  11. customcrystallised at reduced temperature
  12. custommelt at 50°-52° C
  13. custom53% of the theoretical yield)

出典と根拠

ORDレコード
ord-46ce6d20a2594cf7bbc9b814ea0e6854
出典データセット
uspto-grants-1991_03
特許番号
US04997941

反応ノート

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