Hydrochloric Acid → 2-(4-Fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

HRID 1708013

反応式

HRID 1708013 の反応式
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:3]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.Cl.CO[CH:23](OC)[CH2:24][CH:25](OC)OC.C(=O)(O)[O-].[Na+]>C(O)C.[Cl-].[Zn+2].[Cl-]>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[C:3]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:2]3[N:1]=[CH:23][CH:24]=[CH:25][N:6]3[N:5]=2)=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 66019TetramethoxypropaneHCID 516892Sodium BicarbonateHCID 178509109HCID 178509109、化合物

生成物 1

HCID 199572802-(4-Fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine収率 87.6%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 702Ethanol溶媒

実験手順

To a solution of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (102 mg) in ethanol (3 ml) were added concentrated hydrochloric acid (50 μl), zinc chloride (27 mg) and 1,1,3,3-tetramethoxypropane (72 mg) in that order. The mixture was refluxed for one hour, cooled, and poured into an aqueous saturated sodium bicarbonate solution. The separated oil was extracted with dichloromethane. The extract was washed with brine, dried and concentrated in vacuo. The residue was crystallized from a mixture of ethyl acetate and diethyl ether to yield 2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (102 mg).

後処理

  1. temperatureThe mixture was refluxed for one hour
  2. temperaturecooled
  3. extractionThe separated oil was extracted with dichloromethane
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from a mixture of ethyl acetate and diethyl ether

出典と根拠

ORDレコード
ord-3467c19547744fbcbaa5df5a9ba9697c
出典データセット
uspto-grants-1994_10
特許番号
US05356897

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