N,N-Dimethylethylenediamine → HCID 18767659, compound

HRID 2105659Notes

Reaction equation

HRID 2105659 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[CH2:22][C:18]([CH:23]=O)([CH2:19][CH2:20][CH2:21]3)[CH2:17][CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C(O)(=O)C.C(OCC)(=O)C>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH:33][CH2:23][C:18]12[CH2:22][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:25])[N:3]([CH2:26][CH2:27][CH3:28])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:21][CH2:20][CH2:19]1)[CH2:15][CH2:16][CH2:17]2

Participants

7

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 18767627HCID 18767627, compound

Product 1

HCID 18767659HCID 18767659, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.3.1]nonane-1-carbaldehyde (40 mg) taken in 5 ml of CH2Cl2. N1,N1-Dimethyl-ethane-1,2-diamine (40 mg), Na(OAc)3BH (100 mg), 2 drops of Acetic acid were added and stirred at rt overnight. Next day the reaction mixture was diluted with ethyl acetate, washed with sat. NAHCO3, brine and dried over MgSO4. The solvent was removed under reduced pressure. The crude product was purified by Preparative HPLC. Mass (ES+ 459)

Workup

  1. washwashed with sat. NAHCO3, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe crude product was purified by Preparative HPLC

Sources & evidence

ORD record
ord-636aa49ef6964749bd54aecd3646276f
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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