Acetic Anhydride → HCID 67538732, compound

HRID 45159Notes

Reaction equation

HRID 45159 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1COCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:28](=[O:30])[CH3:29])[CH:21]=[CH:20]3)[CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 593942601H-Indole, 5-[[6-[(phenylmethoxy)methyl]-4-pyrimidinyl]oxy]-

Product 1

HCID 67538732HCID 67538732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-1H-indole (12 g, 36.2 mmol) in THF (300 mL), NaH (1.74 g, 43.5 mmol) and acetic anhydride (5.13 mL, 54.3 mmol) are added. After 1 h the reaction is quenched with aqueous ammonium chloride and extracted with EtOAc. Most of the impurities are removed passing it through a silica gel column eluting with 50:50 heptane:EtOAc to give crude 1-[5-(6-benzyloxymethyl-pyrimidin-4-yloxy)-indol-1-yl]-ethanone. This is then dissolved in TFA (300 mL) and heated to 100° C. for 6 hours. At this point the solvent is removed and 1-[5-(6-hydroxymethyl-pyrimidin-4-yloxy)-indol-1-yl]-ethanone isolated via FCC eluting with EtOAc. MS (ESI) m/z 284.0 (M+1).

Workup

  1. customAfter 1 h the reaction is quenched with aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. customMost of the impurities are removed
  4. washeluting with 50:50 heptane

Sources & evidence

ORD record
ord-86d1f7e675fc4d5e9f2355eaaea053c6
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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