Propargyl alcohol → HCID 178456481, compound

HRID 480153Notes

Reaction equation

HRID 480153 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][OH:24])([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].ClN1[C:34](=[O:35])[CH2:33][CH2:32]C1=O.C(O)C#C.CCN(CC)CC>CN(C=O)C>[OH:35][CH2:34][C:33]1[O:24][N:23]=[C:22]([C:17]23[CH2:20][CH2:21][C:14]([C:7]4[NH:8][C:9]5[N:10]([CH2:11][CH2:12][CH3:13])[C:2](=[O:1])[N:3]([CH2:26][CH2:27][CH3:28])[C:4](=[O:25])[C:5]=5[N:6]=4)([CH2:19][CH2:18]2)[CH2:15][CH2:16]3)[CH:32]=1

Participants

6

Reactant 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 178456485HCID 178456485, compound

Product 1

HCID 178456481HCID 178456481, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution 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 (87 mg, 0.22 mmol) and N-chloro succinimide (1.2 eq, 0.27 mmol, 36 mg) in DMF (6 ml) was heated in an oil bath at 60° C. for 1.5 h. The reaction flask was removed from the bath and allowed to cool to rt and propargyl alcohol (2.0 eq, 0.44 mmol, 25 mg) was added. The flask was returned to the oil bath, Et3N (2.0 eq, 0.44 mmol, 44 mg) was added over a period of 15 minutes and the resulting mixture was heated at 60° C. for 3.5 h. The cool reaction mixture was evaporated in vacuo to afford a solid residue that was purified by radial chromatography (2 mm plate) using a gradient of 2-10% MeOH in CH2Cl2 as eluent. Product-containing fractions were combined and concentrated to afford 31 mg (26%) of a white solid. MS: 442 (MH+).

Workup

  1. customThe reaction flask was removed from the bath
  2. additionwas added over a period of 15 minutes
  3. temperaturethe resulting mixture was heated at 60° C. for 3.5 h
  4. customThe cool reaction mixture
  5. customwas evaporated in vacuo
  6. customto afford a solid residue that
  7. customwas purified by radial chromatography (2 mm plate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-38ec5f25dd374a77bdadfa9037acc8a4
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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