Ethyl Acetate → 2-Chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169552Notes

Reaction equation

HRID 2169552 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[NH:8][C:7](=O)[CH:6]3[CH2:14][O:15][CH2:16][CH2:17][N:5]3[C:4]=2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:11]=[C:10]([CH3:12])[C:9]2[NH:8][CH2:7][CH:6]3[CH2:14][O:15][CH2:16][CH2:17][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 866700992-chloro-4-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 866701002-Chloro-4-methyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridineYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A round-bottom flask was charged with 2-chloro-4-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (387 mg, 1.520 mmol) in THF (7.6 mL). To the resulting suspension was added lithium aluminum hydride in THF (1.0 M, 1975 μL, 1.975 mmol) dropwise at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. Ethyl acetate (˜1 mL) was subsequently added in portions at 0° C. Aqueous saturated NH4Cl (5 mL) was then added dropwise until bubbling stopped. The upper organic layer was decanted, concentrated, and then partitioned between brine and ethyl acetate. The murky bottom layer was extracted with ethyl acetate (3×) and the combined organic layers were dried over MgSO4, filtered, and concentrated. The product was triturated with ether/EtOAc and filtered under N2 to give the title compound as a yellow solid (264 mg, 72%). ESI-MS m/z [M+H]+ calc'd for C10H13ClN4O, 241.08; found 241.6.

Workup

  1. customuntil bubbling
  2. customThe upper organic layer was decanted
  3. concentrationconcentrated
  4. custompartitioned between brine and ethyl acetate
  5. extractionThe murky bottom layer was extracted with ethyl acetate (3×)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was triturated with ether/EtOAc
  10. filtrationfiltered under N2

Sources & evidence

ORD record
ord-372c0a9ea2304e24883952099310bf9f
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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