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Dimethyl Sulfate → 2-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-9-methyl-9H-purin-6-amine

HRID 928175
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HRID 928175 반응식
[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][C:12]2[C:13]([O:18][CH3:19])=[N:14][N:15]([CH3:17])[CH:16]=2)[N:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O1CCOCC1>[F:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:20])=[C:4]([NH:11][C:12]2[C:13]([O:18][CH3:19])=[N:14][N:15]([CH3:17])[CH:16]=2)[N:3]=1
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참가 물질

5

반응물 3

HCID 6497Dimethyl Sulfate2회HCID 11430Potassium Carbonate2회HCID 178494310HCID 178494310, 화합물

생성물 1

HCID 1180735462-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-9-methyl-9H-purin-6-amine수율 84.2%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To a vigorously stirred suspension of 2-fluoro-N-(3-methoxy-1-methyl-1H-pyrazol-4-yl)-9H-purin-6-amine (7.25 g, 27.5 mmol, 1.00 eq) and potassium carbonate (7.61 g, 55.1 mmol, 2.00 eq) in 1,4-dioxane (92.0 mL), was added dimethyl sulfate (2.90 mL, 30.3 mmol, 1.10 eq) in a dropwise manner over 3 min. After 4 hr, additional portions of 1,4-dioxane (50.0 mL), potassium carbonate (3.80 g, 27.5 mmol, 1.00 eq), and dimethyl sulfate (1.00 mL, 10.4 mmol, 0.30 eq) were added to the reaction mixture. After a further 16 hr, the reaction mixture was concentrated in vacuo, diluted with water (120 mL), and stirred at ambient temperature for 1 hr. The resulting solids were filtered, washed with water (20 mL), and dried for 16 hr at 60° C. to give the title compound (6.42 g, 84% yield, >95% purity) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (br. s., 1 H) 8.13 (br. s., 1 H) 7.67 (s, 1 H) 3.78 (s, 3 H) 3.70 (s, 3 H) 3.69 (br. s., 3 H). m/z (APCI+) for C11H13FN7O 278.2 (M+H)+.

후처리

  1. waitAfter a further 16 hr
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additiondiluted with water (120 mL)
  4. filtrationThe resulting solids were filtered
  5. washwashed with water (20 mL)
  6. customdried for 16 hr at 60° C.

출처 및 근거

ORD 기록
ord-96b0720b1eb2450a9d865699f928c448
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290496B2

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