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Potassium Carbonate → 4-(2-Aminopyrimidin-5-yl)-2,3-difluorobenzoic acid

HRID 500266
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인쇄 미리보기

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HRID 500266 반응식
OB(O)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[C:4]=1[F:13].Br[C:16]1[CH:17]=[N:18][C:19]([NH2:22])=[N:20][CH:21]=1.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>[NH2:22][C:19]1[N:20]=[CH:21][C:16]([C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:12])[C:4]=2[F:13])=[CH:17][N:18]=1
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참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 532167464-Borono-2,3-difluorobenzoic acid

생성물 1

HCID 672252574-(2-Aminopyrimidin-5-yl)-2,3-difluorobenzoic acid

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매
HCID 702
Ethanol
용매
HCID 962Water용매
HCID 1140Toluene용매

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온도
110 °C

실험 절차

A mixture of 4-(dihydroxyboryl)-2,3-difluorobenzoic acid (0.47 g, 2.3 mmol), 5-bromopyrimidin-2-amine (0.44 g, 2.6 mmol), tetrakis(triphenylphosphine)palladium (0.1 g, 0.1 mmol), and potassium carbonate (0.96 g, 7.0 mmol) in toluene (4.0 mL), ethanol (2.0 mL) and water (2.0 mL) was heated at 110° C. for 3 h. After cooling to RT, the mixture was washed with ether to remove impurity. The aqueous layer was adjusted to pH 6 with 1N HCl. The solid was filtered, washed with water and ether to give the desired product. LCMS: (M+H)=252.9.

후처리

  1. temperatureAfter cooling to RT
  2. washthe mixture was washed with ether
  3. customto remove impurity
  4. filtrationThe solid was filtered
  5. washwashed with water and ether

출처 및 근거

ORD 기록
ord-b90257f63da64419a42d9344cc5dc379
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07767675B2

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