Sodium Methoxide → HCID 59395385, compound

HRID 1097710Notes

Reaction equation

HRID 1097710 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=O)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4].O[NH:26][C:27]([C:29]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1)=[NH:28].C[O-].[Na+]>CO>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][C:19]2[O:21][N:28]=[C:27]([C:29]3([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:30][CH2:31][CH2:32][CH2:33]3)[N:26]=2)[C:6]1=[O:24])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 59395861Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoateHCID 178513213HCID 178513213, compound

Product 1

HCID 59395385HCID 59395385, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)butanoate (53 mg, 0.15 mmol), N-hydroxy-1-phenylcyclopentanecarboximidamide (34 mg, 0.165 mmol) and sodium methoxide (20 mg, 0.37 mmol) in dry MeOH (0.75 ml) were heated at 140° C. in the microwave reactor for 10 min. The mixture was then partitioned between ethyl acetate and 2M HCl, the organic phase evaporated and the product purified by MDAP to give the title compound as a solid (29.1 mg).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and 2M HCl
  2. customthe organic phase evaporated
  3. customthe product purified by MDAP

Sources & evidence

ORD record
ord-3fb90935ec09472bb347478c59227c58
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

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