Sodium hydride → 1,3-Dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201180노트

반응식

HRID 2201180 반응식
[H-].[Na+].[CH3:3][N:4]1[C:9]2=[CH:10][NH:11][CH:12]=[C:8]2[C:7](=[O:13])[N:6]([CH3:14])[C:5]1=[O:15].[CH3:16][Si:17]([CH2:20][CH2:21][O:22][CH2:23]Cl)([CH3:19])[CH3:18]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1COCC1>[CH3:3][N:4]1[C:9]2=[CH:10][N:11]([CH2:23][O:22][CH2:21][CH2:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:12]=[C:8]2[C:7](=[O:13])[N:6]([CH3:14])[C:5]1=[O:15]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 717861851,3-dimethyl-1,6-dihydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione2회

생성물 1

HCID 867229251,3-Dimethyl-6-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% in mineral oil, 335 mg, 8.4 mmol) was added to an ice cooled partial suspension of 1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Intermediate F step 2) (1.00 g, 5.6 mmol), SEM-Cl (1.485 mL, 8.4 mmol) and benzyl triethylammonium chloride (76 mg, 0.34 mmol) in THF (15 mL). The mixture was allowed to reach room temperature slowly and was stirred for 18 hours. The reaction mixture was quenched cautiously with sat ammonium chloride solution (80 mL, added dropwise), then was extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with water (1×40 mL), brine (1×40 mL) then dried with magnesium sulfate and the solvent was removed under vacuum. The residue was triturated with iso-hexane and was dried under vacuum at 50° C.

후처리

  1. customto reach room temperature
  2. customThe reaction mixture was quenched cautiously with sat ammonium chloride solution (80 mL
  3. additionadded dropwise),
  4. extractionthen was extracted with ethyl acetate (3×40 mL)
  5. washThe combined organic layers were washed with water (1×40 mL), brine (1×40 mL)
  6. dry with materialthen dried with magnesium sulfate
  7. customthe solvent was removed under vacuum
  8. customThe residue was triturated with iso-hexane
  9. customwas dried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-4fe20f63ddb146bdb23462d69ddd3cfa
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359381B2

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