Triacetoxyperiodinane → HCID 86665100, compound

HRID 1038818Notes

Reaction equation

HRID 1038818 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[CH2:13][CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.ClC1N=C(Cl)C2OC=CC=2N=1.N1CCC(CO)CC1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[CH2:13][CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 4207714-PiperidinemethanolHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 86665105HCID 86665105, compound

Product 1

HCID 86665100HCID 86665100, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A flask was charged with (1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methanol (11.2 g, 41.8 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [Arkpharm], piperidin-4-ylmethanol), DCM (200 mL) and Dess-Martin periodinane (18.6 g, 43.9 mmol). The mixture was stirred at rt for about 3 h. The mixture was diluted with DCM (100 mL) and washed with an aqueous solution of 1 N Na2CO3 (200 mL). The aqueous layer was extracted with DCM (2×100 mL). The combined extracts were washed with brine, dried over Na2CO3, filtered, and evaporated under vacuum. The residue was purified by column chromatography eluting with 20-80% EtOAc/heptane (120 g silica gel) to provide 1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbaldehyde (10 g, 90%): LC/MS (Table 2, Method u) Rt=1.22 min.; MS m/z: 266 (M+H)+.

Workup

  1. customprepared
  2. washwashed with an aqueous solution of 1 N Na2CO3 (200 mL)
  3. extractionThe aqueous layer was extracted with DCM (2×100 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2CO3
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue was purified by column chromatography
  9. washeluting with 20-80% EtOAc/heptane (120 g silica gel)

Sources & evidence

ORD record
ord-a23a004bfd3747f6b36d41ec6dd2282d
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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