Water → HCID 86651598, compound

HRID 2386281Notes

Reaction equation

HRID 2386281 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.Cl[CH2:18][C:19](=[O:21])[CH3:20].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:18][C:19](=[O:21])[CH3:20])[C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 866515602-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 86651598HCID 86651598, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (822 mg, 3.42 mmol), chloroacetone (0.429 ml, 5.12 mmol) in DMF (10 ml) was added K2CO3 (1.42 g, 10.3 mmol) and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were washed with water and saturated aqueous NaCl, dried and concentrated in vacuo to give a crude solid. The crude residue was triturated with hexane/ethyl acetate (3:1), collected by filtration, rinsed with hexane/ethyl acetate (3:1) and dried to afford 2-chloro-5-(2-oxopropyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (737 mg, 2.48 mmol, 73% yield) as a pale brown solid. MS [M+H] found 297.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with water and saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give a crude solid
  6. customThe crude residue was triturated with hexane/ethyl acetate (3:1)
  7. filtrationcollected by filtration
  8. washrinsed with hexane/ethyl acetate (3:1)
  9. customdried

Sources & evidence

ORD record
ord-34b0d770fc124b8ea19c0f7c01accac5
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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