Pyridine → HCID 136085154, compound

HRID 1194805Notes

Reaction equation

HRID 1194805 reaction equation
[OH:1][CH:2]([CH2:17][OH:18])[CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[OH2:19].[C:20](OC(=O)C)(=[O:22])[CH3:21].N1[CH:32]=[CH:31]C=CC=1>CN(C)C=O>[C:20]([O:1][CH:2]([CH2:17][O:18][C:31](=[O:19])[CH3:32])[CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 136336895HCID 136336895, compound

Product 1

HCID 136085154HCID 136085154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.34 g (20 mmole) of hydrate 9-(2,3-dihydroxy-1-propoxymethyl)guanine, 40 ml of acetic anhydride (increased to 100 ml after several days), 40 ml of pyridine (increased to 80 ml after a few days) and 160 ml of dimethylformamide was stirred at room temperature under a drying tube for a total of 20 days and then concentrated in vacuo. The residue was triturated with 30 ml of methylene chloride and diluted with 100 ml of ether. The solid was collected on a filter, washed with ether, and recrystallized from dioxane-acetic acid to give (after washing with acetone and drying) 4.18 g (62%) of slightly off-white powder, mp 222.5° to 224° C. Structure and purity were confirmed by NMR and TLC (9:1CHCl3 --MeOH).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with 30 ml of methylene chloride
  3. additiondiluted with 100 ml of ether
  4. customThe solid was collected on a filter
  5. washwashed with ether
  6. customrecrystallized from dioxane-acetic acid
  7. customto give
  8. wash(after washing with acetone and drying) 4.18 g (62%) of slightly off-white powder, mp 222.5° to 224° C

Sources & evidence

ORD record
ord-5c6ccb9c541a4cf88b29368acbefd21a
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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