Phosphorus oxychloride → HCID 59299534, compound

HRID 2386633Notes

Reaction equation

HRID 2386633 reaction equation
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([CH2:15][CH:16]=[CH2:17])[C:10]([C:18]([NH2:20])=O)=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].O=P(Cl)(Cl)Cl>CN(C=O)C>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([CH2:15][CH:16]=[CH2:17])[C:10]([C:18]#[N:20])=[N:9][C:8]=2[N:7]([CH2:21][CH2:22][CH2:23][CH3:24])[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59299542HCID 59299542, compound

Product 1

HCID 59299534HCID 59299534, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dibutyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carboxamide (300 mg) in anhydrous DMF (7 ml) at 0° C. was treated dropwise with POCl3 (237 uL). The ice-bath was removed and after 2 hours the mixture was partitioned between water and Et2O. The aqueous layer was re-extracted with Et2O and the combined extracts separated, washed with water (×2), brine, then dried (MgSO4) and concentrated, giving a yellow oil (312 mg). The oil was taken up in cyclohexane and purified by SPE (Si, 10 g) eluting with EtOAc/cyclohexane mixtures. Concentration of the product fractions gave the title compound as a colourless oil (150 mg, 53%); m/z. 330.3 [MH+].

Workup

  1. customThe ice-bath was removed and after 2 hours the mixture
  2. customwas partitioned between water and Et2O
  3. extractionThe aqueous layer was re-extracted with Et2O
  4. customthe combined extracts separated
  5. washwashed with water (×2), brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-527d7cfa752b45edaf4846c5c58b97dc
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

Loading…