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Potassium Carbonate → 5-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine

HRID 1912646
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HRID 1912646 반응식
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].B(O)(O)[C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1>C1(C)C=CC=CC=1.O.COCCOC.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>[CH2:1]([O:8][C:9]1[C:14]([Cl:15])=[N:13][CH:12]=[N:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 583080995-(Benzyloxy)-4,6-dichloropyrimidine

생성물 1

HCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine수율 35.4%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 131731093
PhMe H2O DME
용매

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온도
100 °C

실험 절차

The compound from step 3 (12.78 g, 0.05 mol) was dissolved in (4:1:1) PhMe/H2O/DME (111 ml). Pd(Ph3P)4 (2.9 g, 0.05 eq), K2CO3, and p-tolylboronic acid (6.81 g, 1 eq) were added, the mixture was degassed and heated at 100° C. overnight. After cooling to room temperature the organic layer was purified by silica gel chromatography (0-10% EtOAc in hexane) to give 5.5 g of the title compound.

후처리

  1. customthe mixture was degassed
  2. temperatureAfter cooling to room temperature the organic layer
  3. customwas purified by silica gel chromatography (0-10% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-a992c9aa7d46467f98590f61c2764cf9
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609676B2

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