Sodium hydride → HCID 86723446, compound

HRID 2201205Notes

Reaction equation

HRID 2201205 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:11][CH:12]=[C:13]3[C:18]=2[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]3[CH3:22])[CH:7]=[CH:8][CH:9]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.[CH3:49][C:50]1([CH3:64])[O:54][CH:53]([CH2:55]OS(C(F)(F)F)(=O)=O)[CH2:52][O:51]1>CN(C=O)C>[CH3:49][C:50]1([CH3:64])[O:54][CH:53]([CH2:55][N:11]2[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[CH:5]=3)=[C:18]3[C:13]([N:14]([CH3:22])[C:15](=[O:21])[N:16]([CH3:20])[C:17]3=[O:19])=[CH:12]2)[CH2:52][O:51]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 26541Dibenzo-18-crown-6HCID 105157222,2-Dimethyl-4-(trifluoromethylsulfonyloxymethyl)-1,3-dioxolaneHCID 867229305-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 86723446HCID 86723446, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil) (234 mg, 5.86 mmol) was added portionwise to a solution of 5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Intermediate Nf) (1000 mg, 3.66 mmol) and dibenzo-18-crown-6 (132 mg, 0.366 mmol) in DMF (28.1 mL) at 0° C. The solution was warmed to room temperature and stirred for 20 minutes, then re-cooled to 0° C. (2,2-Dimethyl-1,3-dioxolan-4-yl)methyltrifluoromethane sulfonate (Intermediate Sb) (1547 mg, 5.86 mmol) was added dropwise over 5 minutes. The mixture was warmed to room temperature and stirred for 3 hours. The reaction was quenched with saturated NH4Cl(aq) (10 mL) and extracted with DCM (3×30 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum to afford the title compound as a red/brown amorphous solid.

Workup

  1. additionwas added dropwise over 5 minutes
  2. temperatureThe mixture was warmed to room temperature
  3. stirringstirred for 3 hours
  4. customThe reaction was quenched with saturated NH4Cl(aq) (10 mL)
  5. extractionextracted with DCM (3×30 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-28afb79056eb4b05945914dfaae09d13
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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