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Potassium Carbonate → 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide

HRID 1257786
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HRID 1257786 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:27][C:24]1[N:25]=[CH:26][C:21]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=2)=[CH:22][N:23]=1
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8

반응물 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-

생성물 1

HCID 672245484-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide수율 91.4%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매
HCID 702Ethanol용매
HCID 962Water용매
HCID 1140Toluene용매

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온도
110 °C

실험 절차

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (900 mg, 3.9 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (710 mg, 3.2 mmol), tetrakis(triphenylphosphine)palladium (100 mg, 0.1 mmol) and potassium carbonate (1.3 g, 9.7 mmol) in toluene (6.0 mL) and ethanol (3.0 mL) and water (3.0 mL) was heated at 110° C. for 2 hours. After cooling to RT, the reaction mixture was quenched with water and extracted with diethyl ether. The solid was filtered and washed with water and diethyl ether to afford the desired product (720 mg).

후처리

  1. temperatureAfter cooling to RT
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with diethyl ether
  4. filtrationThe solid was filtered
  5. washwashed with water and diethyl ether

출처 및 근거

ORD 기록
ord-bb0e185e61f544f5a8410172b71fdb8a
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461330B2

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