Ethyl Acetate → HCID 86651562, compound

HRID 2386237Notes

Reaction equation

HRID 2386237 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3([CH3:17])[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.Br[CH2:19][CH:20]1[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CS(C)=O.O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:19][CH:20]3[CH2:22][CH2:21]3)[C:7](=[O:12])[C:6]3([CH3:17])[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 781653422-chloro-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 86651562HCID 86651562, compoundYield 131.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Chloro-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.846 g, 3.32 mmol) and (bromomethyl)cyclopropane (0.672 g, 4.98 mmol) were mixed in DMSO (5 ml). Potassium carbonate (0.918 g, 6.64 mmol) was added. The mixture was stirred for 30 minutes at room temperature and then for 2 hours at 35° C. EtOAc (40 ml) was added followed by addition of water (30 ml). Aqueous phase was separated and extracted with EtOAc (2×30 ml). The combined organic phase was washed with water (2×20 ml). The organic solution was concentrated to near dryness at which point a solid had precipitated out. EtOAc (5 ml) and hexanes (20 ml) were added and the mixture was stirred for 20 minutes. The solid was collected by filtration to afford 1.35 g product as a white solid. Concentration and crystallization of mother liquor afforded another 0.28 g of compound as second crop. 1H NMR (400 MHz, CDCl3) δ=0.34 (m, 2H), 0.46 (m, 2H), 1.13 (m, 1H), 1.39 (s, 3H), 3.21 (m, 1H), 3.55 (m, 1H), 3.66 (d, 1H), 3.77 (m, 1H), 3.85-4.02 (m, 4H), 8.20 (s, 1H)

Workup

  1. waitfor 2 hours at 35° C
  2. customAqueous phase was separated
  3. extractionextracted with EtOAc (2×30 ml)
  4. washThe combined organic phase was washed with water (2×20 ml)
  5. concentrationThe organic solution was concentrated
  6. customhad precipitated out
  7. additionEtOAc (5 ml) and hexanes (20 ml) were added
  8. stirringthe mixture was stirred for 20 minutes
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-e617551196a942339f9d4b6846ecc4b3
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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