Water → HCID 178456484, compound

HRID 480143Notes

Reaction equation

HRID 480143 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 Na2SO4, 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 Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6092e80536ab4512be5d8631791f3fc3
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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