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

HRID 624605Notes

Reaction equation

HRID 624605 reaction equation
[H-].[Na+].NC[CH2:5][N:6]1[C:14](C2C=CC=C(Cl)C=2)=[C:13]2[C:8]([N:9]([CH3:25])[C:10](=[O:24])[N:11]([CH3:23])[C:12]2=[O:22])=[CH:7]1.[CH3:26][Si:27]([CH2:30][CH2:31][O:32]CCl)([CH3:29])[CH3:28]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1COCC1>[CH3:25][N:9]1[C:8]2=[CH:7][N:6]([CH2:5][O:32][CH2:31][CH2:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[CH:14]=[C:13]2[C:12](=[O:22])[N:11]([CH3:23])[C:10]1=[O:24]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 867228806-(2-Amino-ethyl)-5-(3-chloro-phenyl)-1,3-dimethyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-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 B step 1) (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 dried under vacuum at 50° C. to afford the title compound.

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. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-99e3ea4b61ef49c6996ba6c3708ebe64
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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