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Diethyl Ether → 7-(4'-Fluorophenyl)-6-hydroxymethyl-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidin

HRID 846593
ノート
印刷プレビュー

反応式

HRID 846593 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([CH3:17])[CH:16]=[C:12]3[N:11]=[C:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2[C:21](OCC)=[O:22])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+].C(OCC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]3[N:14]=[C:15]([CH3:17])[CH:16]=[C:12]3[N:11]=[C:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2[CH2:21][OH:22])=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 14994686Ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl)pyrazolo[1,5-a]pyrimidin-6-ylcarboxylateHCID 86583787Diisobutylaluminumhydride toluene

生成物 1

HCID 149946877-(4'-Fluorophenyl)-6-hydroxymethyl-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidin収率 84%

試薬・触媒・溶媒

1
HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

4.40 g (12.9 mmol) of ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl)pyrazolo [1,5-a]pyrimidin-6-ylcarboxylate was dissolved in 40 ml of dry toluene under a nitrogen atmosphere and cooled to 0° C. in an ice bath. To this solution, 33 ml of a 16 weight % diisobutylaluminium hydride-toluene solution was dropwise added, and then, the mixture was stirred at 0° C. for one hour. After confirming the complete disappearance of ethyl 7-(4'-fluorophenyl)-2-methyl-5-(1'-methylethyl) pyrazolo[1,5-a]pyrimidin-6-ylcarboxylate by thin layer chromatography, a saturated ammonium chloride aqueous solution was added thereto at 0° C. to terminate the reaction. Diethyl ether was added to the reaction mixture, and the organic layer was separated. The gelled substance was dissolved by an addition of a sodium hydroxide aqueous solution and newly extracted with ethyl ether. The ethyl ether extracts were put together and dried over anhydrous magnesium sulfate. The extract was subjected to filtration, and the solvent was distilled off and the residue was recrystallized from ethyl acetate to obtain 3.24 g (yield: 84%) of the slightly yellow desired compound.

後処理

  1. customat 0° C. to terminate
  2. customthe reaction
  3. customthe organic layer was separated
  4. dissolutionThe gelled substance was dissolved by an addition of a sodium hydroxide aqueous solution
  5. extractionnewly extracted with ethyl ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe extract was subjected to filtration
  8. distillationthe solvent was distilled off
  9. customthe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-7c6be4a211d54445a890a98d33c97a10
出典データセット
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05137891

反応ノート

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