Acetic Acid → HCID 178508945, compound

HRID 380444Notes

Reaction equation

HRID 380444 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1N2CC[N:13](CC2)C1.[N:19]1[CH:27]=[C:26]2[C:22]([N:23]=[CH:24][NH:25]2)=[N:21][CH:20]=1.C(O)(=O)C>CS(C)=O>[CH:5]1[CH:4]=[CH:3][C:2]([CH2:1][O:8][C:27]2[C:26]3[N:25]=[CH:24][NH:23][C:22]=3[N:21]=[C:20]([NH2:13])[N:19]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 69727605DABCO purine

Product 1

HCID 178508945HCID 178508945, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Benzyl alcohol (215 mg, 1.99 mmol) was added to sodium hydride (0.017 g, 0.71 mmol) in anhydrous DMSO (0.4 ml). After 1 h ‘DABCO-purine’ (0.10 g, 0.36 mmol) was added and the reaction stirred for 48 h at room temperature. Acetic acid (0.06 ml) was added and the solvents removed in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 10% methanol in dichloromethane. The title compound was collected as a white solid (69 mg, 81%). λmax (CH3OH)/nm 285; δH (200 MHz, d6-DMSO) 7.96 (1H, s, C(8)H), 7.40 (5H, m, Ph), 6.44 (2H, s, NH2), 5.61 (2H, s, OCH2).

Workup

  1. customthe solvents removed in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with 10% methanol in dichloromethane
  4. customThe title compound was collected as a white solid (69 mg, 81%)

Sources & evidence

ORD record
ord-f0307e0896b641b1b24d8051a15d0522
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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