Tricalcium Phosphate → 3-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester

HRID 1443840노트

반응식

HRID 1443840 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]2[N:12]=[CH:13][C:14](Br)=[C:8]2[N:7]=1)=[O:5])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19](OB(O)O)[CH:20]=[CH:21][CH:22]=1.P([O-])([O-])([O-])=O.[Ca+2].P([O-])([O-])([O-])=O.[Ca+2].[Ca+2].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]2[N:12]=[CH:13][C:14]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[CH:22]=3)=[C:8]2[N:7]=1)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 24456Tricalcium PhosphateHCID 312751,4-DioxaneHCID 22494354m-Chlorophenylboric acidHCID 68692447Ethyl 3-bromopyrazolo[1,5-a]pyrimidine-5-carboxylate

생성물 1

HCID 586288723-(3-Chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester수율 89.8%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

A mixture of 3-bromo-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester (18.00 g), 3-chlorophenyl boric acid (12.50 g), calcium phosphate (31.12 g), and 200 ml of dioxane was stirred under a nitrogen atmosphere, added with tetrakis(triphenylphosphine) palladium (0) (1.50 g), and heated at reflux over 3 hours. The reactant was cooled to room temperature, and thereafter poured into 150 ml of water, and extracted with 300 ml of toluene. The extract was washed with saturated saline solution, dried with magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=8:2) to yield 3-(3-chlorophenyl)-pyrazolo-[1,5-a]-pyrimidine-5-carboxylic acid ethyl ester (18.05 g, 89%) as a brown columnar crystal. mp: 126-129° C.

후처리

  1. temperatureheated
  2. temperatureat reflux over 3 hours
  3. extractionextracted with 300 ml of toluene
  4. washThe extract was washed with saturated saline solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:toluene=8:2)

출처 및 근거

ORD 기록
ord-8ed00fc09b824d49a03b196ae397820c
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662826B2

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