Dimethyl Sulfoxide → HCID 86651573, compound

HRID 1696004Notes

Reaction equation

HRID 1696004 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:14][CH2:13]3)[C:7](=[O:15])[CH:6]3[CH2:16][O:17][CH2:18][CH2:19][N:5]3[C:4]=2[N:3]=1.[CH3:20]S(C)=O.IC.CC([O-])(C)C.[Na+]>O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:13][CH2:14]3)[C:7](=[O:15])[C:6]3([CH3:20])[CH2:16][O:17][CH2:18][CH2:19][N:5]3[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 86651572HCID 86651572, compound

Product 1

HCID 86651573HCID 86651573, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask equipped with a magnetic stirrer was added 2-chloro-5-cyclopropyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (121 mg, 0.431 mmol), DMSO (2 ml), and iodomethane (0.032 ml, 0.517 mmol). The mixture was cooled to 0° C. and added sodium 2-methylpropan-2-olate (49.7 mg, 0.517 mmol) and allowed to stir at 20° C. for 16 hours. The reaction solution was suspended in water, and the precipitate filtered. The collected solid was washed successively with small amount of ethanol and diethyl ether. The solid was collected and dried in-vacuo to afford 2-chloro-5-cyclopropyl-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (100 mg, 0.339 mmol, 79% yield) as a tan solid. MS [M+H] found 295.

Workup

  1. customA round-bottomed flask equipped with a magnetic stirrer
  2. filtrationthe precipitate filtered
  3. washThe collected solid was washed successively with small amount of ethanol and diethyl ether
  4. customThe solid was collected
  5. customdried in-vacuo

Sources & evidence

ORD record
ord-bd069e082cb54c8c920ec4c391317e59
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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