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

HRID 2201180Notes

Reaction equation

HRID 2201180 reaction equation
[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]

Participants

6

Reactant 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)-dione2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-4fe20f63ddb146bdb23462d69ddd3cfa
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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