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Methanol → 2,4-Bis(methyloxy)-5-(4-methyl-1,3-thiazol-2-yl)pyrimidine

HRID 1925038
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HRID 1925038 반응식
I[C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.C(=O)(O)[O-].[Na+].[CH3:13][O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18](B(O)O)=[CH:17][N:16]=1.CO>COCCOC.C(Cl)Cl.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>[CH3:13][O:14][C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18]([C:2]2[S:3][CH:4]=[C:5]([CH3:7])[N:6]=2)=[CH:17][N:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 231545942-Iodo-4-methyl-1,3-thiazole

생성물 1

HCID 594483702,4-Bis(methyloxy)-5-(4-methyl-1,3-thiazol-2-yl)pyrimidine수율 106.2%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6344Dichloromethane용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

2-iodo-4-methyl-1,3-thiazole (prepared according to procedure described in JACS 123 (6), 1017-1022, (2001), 250 mg, 1.111 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (4.629 ml). Pd(Ph3P)4 (64.2 mg, 0.056 mmol) was added and the mixture was stirred at room temperature for 10 minutes. 1M aqueous sol. Sodium bicarbonate (4.443 ml, 4.44 mmol) and [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (409 mg, 2.222 mmol) were added and the resulting mixture was stirred at 85° C. for 2 hours. The mixture was allowed to cool to rt and it was diluted with DCM (5 mL). The aqueous was separated and extracted with DCM (2×5 mL). The organics were combined and dried (Na2SO4 then rotaevaporator) to give a yellow solid that was purified by silica chromatography (Biotage SP1, 25+M), eluting with DCM:MeOH from 100:0 to 9:1 to afford the title compound as a pale yellow solid (280 mg, 78% yield).

후처리

  1. stirringthe resulting mixture was stirred at 85° C. for 2 hours
  2. temperatureto cool to rt
  3. customThe aqueous was separated
  4. extractionextracted with DCM (2×5 mL)
  5. dry with materialdried (Na2SO4
  6. customto give a yellow solid
  7. customthat was purified by silica chromatography (Biotage SP1, 25+M)
  8. washeluting with DCM

출처 및 근거

ORD 기록
ord-f8552351a1444f3b960d00fe19895fad
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178549B2

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