Dichloromethane → HCID 58972435, compound

HRID 2264396Notes

Reaction equation

HRID 2264396 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[CH:9]=[N:8][C:7](N)=[N:6][C:5]=2[C:4]([CH3:13])([CH3:12])[O:3]1.N([O-])=O.[Na+].[Cl:19]CCl>Cl.[Cl-].[Zn+2].[Cl-]>[Cl:19][C:7]1[N:8]=[CH:9][C:10]2[C:2]([CH3:14])([CH3:1])[O:3][C:4]([CH3:13])([CH3:12])[C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 23668193Sodium NitriteHCID 68785241HCID 68785241, compound

Product 1

HCID 58972435HCID 58972435, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 5,5,7,7-tetramethyl-5,7-dihydro-furo[3,4-d]pyrimidin-2-ylamine (38.6 g, 200.0 mmol, 1.0 equiv) in dichloromethane (80 mL) and 37% HCl (70 mL) at 0° C. was added zinc(II) chloride (46.3 g, 340.0 mmol, 1.7 equiv) in portions within 30 min. After the addition was completed, sodium nitrite (23.5 g, 340.0 mmol, 1.7 equiv) was added slowly within 3 h keeping the reaction temperature below 5° C. After stirring for an additional time period of 1 h, the reaction mixture was poured on ice and then extracted with dichloromethane (3×200 mL), the combined organic phases washed with a sat. solution of sodium carbonate (2×100 mL), dried over MgSO4 and concentrated by evaporation under reduced pressure. The reaction product was dissolved in diethyl ether (200 mL), filtered and the organic solvent removed by evaporation under reduced pressure yielding 33.2 g (78%) of the title compound. MS (EI): 213 [M]+.

Workup

  1. additionAfter the addition
  2. customthe reaction temperature below 5° C
  3. additionthe reaction mixture was poured on ice
  4. extractionextracted with dichloromethane (3×200 mL)
  5. washthe combined organic phases washed with a sat. solution of sodium carbonate (2×100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated by evaporation under reduced pressure
  8. dissolutionThe reaction product was dissolved in diethyl ether (200 mL)
  9. filtrationfiltered
  10. customthe organic solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-565e3e95dfdd4fbdb718a0f1fefd871c
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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