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Water → 3-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester

HRID 1409997
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HRID 1409997 반응식
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:22][O:23][C:24](=[O:40])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.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>[CH3:22][O:23][C:24](=[O:40])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:2]2[N:3]=[C:4]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=2)[CH:26]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 715341855-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

생성물 1

HCID 683794533-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester수율 81%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of (5-chloro-thiazolo[5,4-d]pyrimidin-7-yl)-(3,4-dimethoxy-phenyl)-amine (0.90 g, 2.79 mmol) and 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (0.95 g, 3.62 mmol) in 100 mL of 1,4-dioxane were added Na2CO3 (0.93 g, 8.8 mmol) and 5 mL of water at room temperature. Then the mixture was degassed with nitrogen for 15 minutes. Pd(PPh3)4 (0.32 g, 0.279 mmol) was added in one portion and the reaction mixture was stirred at 100° C. for 16 hours under nitrogen. The solvent was evaporated and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, CH2Cl2:methanol=100:1) to give 3-[7-(3,4-dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid methyl ester (0.95 g, 81%) as a yellow sold. LC-MS: 423.1 [M+H]+, tR=1.68 min.

후처리

  1. customThen the mixture was degassed with nitrogen for 15 minutes
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel chromatography (silica gel 200-300 mesh, CH2Cl2:methanol=100:1)

출처 및 근거

ORD 기록
ord-64036bf4bfa6439498becfbb12fadfef
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921383B2

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