Hydrochloric Acid → HCID 86651593, compound

HRID 2386274Notes

Reaction equation

HRID 2386274 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]([CH3:22])([O:15]C3CCCCO3)[CH3:14])[C:7](=[O:23])[C:6]3([CH3:28])[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]=2[N:3]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]([OH:15])([CH3:22])[CH3:14])[C:7](=[O:23])[C:6]3([CH3:28])[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86651592HCID 86651592, compound

Product 1

HCID 86651593HCID 86651593, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-6a-methyl-5-(2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (133 mg, 0.322 mmol) in THF (3 ml) was added 1 N HCl aqueous solution (1 ml, 1.000 mmol) and the reaction mixture was stirred for 1 h, followed by being poured into NaHCO3 aqueous solution. Extraction with EtOAc, drying over Na2SO4 and concentration in vacuo gave crude 2-chloro-5-(2-hydroxy-2-methylpropyl)-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (84.9 mg, 0.260 mmol, 81% yield) as a yellow oil which was used in the next step without further purification. MS [M+H] found 327.

Workup

  1. extractionExtraction with EtOAc
  2. dry with materialdrying over Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-2d5c49b2570d498180a736a3f8c764dd
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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