Chlorosuccinimide → HCID 25061714, compound

HRID 1664514Notes

Reaction equation

HRID 1664514 reaction equation
[CH3:1][C:2]1[N:6]2[C:7](=[O:19])[C:8]3[NH:9][CH:10]=[N:11][C:12]=3[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]2=[N:4][N:3]=1.[Cl:20]N1C(=O)CCC1=O>C1COCC1>[Cl:20][C:10]1[NH:9][C:8]2[C:7](=[O:19])[N:6]3[C:2]([CH3:1])=[N:3][N:4]=[C:5]3[N:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57600225HCID 57600225, compound

Product 1

HCID 25061714HCID 25061714, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (0.10 g, 0.38 mmol) in THF (5 mL) in a microwave reaction tube was added N-chlorosuccinimide (0.046 g, 0.42 mmol). The mixture was heated at 70° C. in a microwave oven for 20 min. After cooling to room temperature, it was purified using preparative LCMS to provide the product (0.021 g). 1HNMR (300 MHz, CD3OD): δ 4.39 (t, J=7.5 Hz, 2H), 2.46 (s, 3H), 1.91 (m, 2H), 1.39 (m, 4H), 0.92 (m, 3H). LCMS calculated for C12H16ClN6O (M+H): 295.1. found: 295.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. customit was purified

Sources & evidence

ORD record
ord-680b0804a79f4f4ca449a0592f533040
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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