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Sodium Carbonate → Methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate

HRID 1410046
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HRID 1410046 반응식
Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=2)[C:33]([O:35][CH3:36])=[O:34])O1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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>[CH3:21][S:18]([C:14]1[CH:13]=[C:12]([NH:11][C:4]2[C:5]3[N:10]=[CH:9][S:8][C:6]=3[N:7]=[C:2]([C:30]3[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=3)[C:33]([O:35][CH3:36])=[O:34])[N:3]=2)[CH:17]=[CH:16][CH:15]=1)(=[O:20])=[O:19]
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참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 866717835-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

생성물 1

HCID 66549139Methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate수율 58%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

실험 절차

Under N2 atmosphere, 5-chloro-N-(3-(methylsulfonyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (200 mg, 0.59 mmol), methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (183 mg, 0.7 mmol), Pd(PPh3)4 (30 mg, 0.026 mmol) and Na2CO3 (127 mg, 1.2 mmol) in 5 mL of water was added into the mixture solvent of 5 mL of water and 50 mL of 1,4-dioxane. The mixture was stirred at reflux for 18 hours. The solvent was removed under reduce pressure and the residue was purified by silica gel chromatography, eluting with petroleum ether and ethyl acetate (3:1) to give methyl 3-(7-(3-(methylsulfonyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate (150 mg, 58%) as a yellow sold. 1H NMR (300 MHz, DMSO): δ 10.76 (s, 1H), 9.45 (s, 1H), 8.99-8.98 (m, 1H), 8.93 (s, 1H), 8.73 (d, 1H, J=7.8 Hz), 8.21-8.18 (m, 1H), 8.09 (d, 1H, J=7.8 Hz), 7.69-7.65 (m, 3H), 3.91 (s, 3H), 3.26 (s, 3H). LC-MS: 441 [M+H]+, 903 [2M+Na]+, 439 [M−H]−, tR=1.61 min. HPLC: 98.78% at 214 nm, 97.72% at 254 nm, tR=8.14 min.

후처리

  1. temperatureat reflux for 18 hours
  2. customThe solvent was removed
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with petroleum ether and ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-c3f65baac0054296a32d6b2df2c03f53
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08921383B2

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