Tetrahydrofuran → 3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester

HRID 395282Notes

Reaction equation

HRID 395282 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17](C=O)([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:24])[NH:3]1.C1(P(=[CH:44][C:45]([O:47][CH3:48])=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:49]1COCC1>>[CH3:48][O:47][C:45](=[O:46])[CH:44]=[CH:49][C:17]12[CH2:16][CH2:15][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:24])[NH:3][C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:19][CH2:18]1)[CH2:21][CH2:20]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 119942814-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

Product 1

HCID 691483283-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester

Procedure

4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde (900 mg, 2.73 mmol) was dissolved in 25 mL of THF and methyl (triphenylphosphoranylidene)acetate (1.83 g, 2 eq) was added. The resulting reaction mixture was stirred under reflux for 18 h. It was then cooled to rt and purified by preparative HPLC using a mixture of aqueous acetonitrile to afford 300 mg of the desired product.

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for 18 h
  3. custompurified by preparative HPLC
  4. additiona mixture of aqueous acetonitrile

Sources & evidence

ORD record
ord-26c440611ac3417ebc5b27fb290846f1
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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