Water → 2-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

HRID 2386217Notes

Reaction equation

HRID 2386217 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.[CH3:17][C:18]([CH3:21])([O-])[CH3:19].[Na+].BrCC1CC1.O>CS(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:17][CH:18]3[CH2:21][CH2:19]3)[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 81503BromomethylcyclopropaneHCID 23676156Sodium t-butoxideHCID 866515602-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 866515612-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (3 g, 12.47 mmol) in DMSO (10 mL) cooled in an ice water bath was added sodium tert-butoxide (1.32 g, 13.7 mmol). After 15 minutes stirring, the mixture was allowed to warm up to room temperature and stirred for 45 minutes. Then (bromomethyl)cyclopropane (1.27 mL, 13 mmol) was added dropwise in 12 minutes and the resulting mixture stirred at room temperature for 15 hours. Water was added and the resulting yellow precipitate was collected by vacuum filtration and washed repeatedly with water. The solid was subjected to vacuum for 4 hours to give 2-chloro-5-(cyclopropylmethyl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one as a yellow solid (3.57 g, 97%). MS [M+H] found 295.2.

Workup

  1. temperaturecooled in an ice water bath
  2. stirringstirred for 45 minutes
  3. stirringthe resulting mixture stirred at room temperature for 15 hours
  4. filtrationthe resulting yellow precipitate was collected by vacuum filtration
  5. washwashed repeatedly with water
  6. waitThe solid was subjected to vacuum for 4 hours

Sources & evidence

ORD record
ord-2d53ee79690e47849cabcd66a969e6a7
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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