2-Thiophenecarboxaldehyde → HCID 67079164, compound

HRID 2105650Notes

Reaction equation

HRID 2105650 reaction equation
[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:20]([N:15]1[C:16](=[O:19])[C:17]2[NH:18][C:10]([C:5]34[CH2:8][CH2:9][C:2]([NH:1][CH2:32][C:28]5[S:27][CH:31]=[CH:30][CH:29]=5)([CH2:7][CH2:6]3)[CH2:3][CH2:4]4)=[N:11][C:12]=2[N:13]([CH2:24][CH2:25][CH3:26])[C:14]1=[O:23])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18767683HCID 18767683, compound

Product 1

HCID 67079164HCID 67079164, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg of 8-(4-Amino-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 20) (0.28 mmol) and 37 mg of thiophene-2-carboxaldehyde (0.33 mmol) in CH2Cl2 (5 ml) was added 5 drops of glacial acetic acid and 100 mg of sodium triacetoxyborohydride (0.47 mmol). Complete conversion occurs over 24 h at rt. The reaction mixture was quenched with 2 ml of ethanol and 2 ml of 2N HCl and then concentrated in vacuo to afford a colorless oil which was purified from anhydrous acetonitrile to afford 50.8 mg (40%) as a white solid (MH+=456.29). The following compounds were prepared in an analogous manner:

Workup

  1. customThe reaction mixture was quenched with 2 ml of ethanol and 2 ml of 2N HCl
  2. concentrationconcentrated in vacuo
  3. customto afford a colorless oil which
  4. customwas purified from anhydrous acetonitrile
  5. customto afford 50.8 mg (40%) as a white solid (MH+=456.29)
  6. customThe following compounds were prepared in an analogous manner

Sources & evidence

ORD record
ord-e0427d27d35c4bcfbda8ca70d1d603ff
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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