Water → HCID 178456484, compound

HRID 2105670Notes

Reaction equation

HRID 2105670 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]34[CH2:21][CH2:20][C:17]([CH:22]=[N:23]O)([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].O=P(Cl)(Cl)Cl.O>C(Cl)(Cl)Cl>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]34[CH2:19][CH2:18][C:17]([C:22]#[N:23])([CH2:20][CH2:21]3)[CH2:16][CH2:15]4)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178456485HCID 178456485, compound

Product 1

HCID 178456484HCID 178456484, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde oxime (400 mg, 1.03 mmol) in CHCl3 (20 ml), cooled with the aid of an ice bath, was added POCl3 (neat, 1.5 eq, 237 mg) and the resulting mixture was allowed to reach ambient temperature overnight (17 h). The reaction mixture was poured into water, the phases were separated and the organic phase was washed with saturated aqueous solution of NaHCO3, dried over NaSO4, filtered and concentrated in vacuo to give a white, brittle foam (360 mg, 95%). MS: 370 (MH+).

Workup

  1. temperaturecooled with the aid of an ice bath
  2. custom(17 h)
  3. customthe phases were separated
  4. washthe organic phase was washed with saturated aqueous solution of NaHCO3
  5. dry with materialdried over NaSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf4d643644c0444d9cb95dfd725bca34
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

Loading…