Water → HCID 22036335, compound

HRID 493342Notes

Reaction equation

HRID 493342 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:16][CH:17]=[CH:18][N:19]=2)=[N:6][CH:7]=[CH:8][N:9]=1.O.[O:34]1CCOC[CH2:35]1>CO>[CH3:35][O:34][C:4]1[C:5]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:16][CH:17]=[CH:18][N:19]=2)=[N:6][CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 312751,4-DioxaneHCID 22036419HCID 22036419, compound

Product 1

HCID 22036335HCID 22036335, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

NaH (50% in mineral oil; 0.010 g, 2.1 mmol) was added to a stirred solution of the product from Step 1 (0.38 g, 0.87 mmol) in dioxane (8 mL) and MeOH (2 mL) in a reaction tube. As the gas evolution had ceased, the tube was sealed and the mixture was stirred at 100° C. for 15 min. The reaction was poured into water and extracted with toluene, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica using toluene/EtOAc (7:3) as eluent to give 0.178 g (47%) of the title product. Pos-EI-MS shows M+ and 11 ions supporting the stated structure. HRMS m/z calcd for C20H28N6O5 (M)+ 432.2121, found 432.2126.

Workup

  1. customthe tube was sealed
  2. extractionextracted with toluene
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-82778150b5e2476eaebc0471d78ab393
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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