N,N-Dimethylethylenediamine → HCID 18767659, compound

HRID 480129Notes

Reaction equation

HRID 480129 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-52ff14068ebc4d66922e0ccd02b2629c
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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