2,5-Dimethoxytetrahydrofuran → HCID 17968239, compound

HRID 271602Notes

Reaction equation

HRID 271602 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:17]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]3[N:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.CO[CH:27]1[CH2:31][CH2:30][CH:29](OC)O1>C(O)(=O)C>[CH3:22][C:19]([CH3:21])([CH3:20])[CH2:18][N:17]1[C:10]2[N:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH:27]=[CH:31][CH:30]=[CH:29]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 59834697HCID 59834697, compound

Product 1

HCID 17968239HCID 17968239, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-(4-amino-benzyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.32 mmol) in acetic acid (1 ml) is slowly added 2,5-dimethoxy-tetrahydro-furan (0.35 mmol). The reaction mixture is refluxed for 2 h and cooled. The mixture is quenched with saturated ammonium chloride and extracted with AcOEt. The organic layer is washed with saturated ammonium chloride and brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a silica gel column chromatography, which is eluted with following solvents: n-hexane:AcOEt=6:1 (v/v) and n-hexane:AcOEt=4:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 60.2%, Rf=0.55 (n-hexane:AcOEt=2:1). 1H-NMR (400 MHz, CDCl3) δ 1.06(s, 9H), 4.09(s, 2H), 4.24(s, 2H), 6.27(s, 1H), 6.35-6.36(m, 2H), 7.16-7.17(m, 2H), 7.21(d, 2H), 7.38(d, 2H), 8.84(s, 1H)

Workup

  1. temperatureThe reaction mixture is refluxed for 2 h
  2. temperaturecooled
  3. customThe mixture is quenched with saturated ammonium chloride
  4. extractionextracted with AcOEt
  5. washThe organic layer is washed with saturated ammonium chloride and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated down
  8. washis eluted with following solvents
  9. customThe solvent of the latter effluent is removed by evaporation
  10. customdried in vacuo

Sources & evidence

ORD record
ord-ee40acaaef474105839a55d758bd2af8
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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