Sodium triacetoxyborohydride → HCID 57384595, compound

HRID 339934Notes

Reaction equation

HRID 339934 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:24])[N:6]2[CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][OH:23].[CH:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:29][CH:28]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.O>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:24])[N:6]2[CH2:16][CH2:17][CH2:18][N:19]([CH2:25][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:31][CH:32]=1)[CH2:20][CH2:21][CH2:22][OH:23]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 113441872-(4-formylphenyl)acetic AcidHCID 67055579HCID 67055579, compound

Product 1

HCID 57384595HCID 57384595, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 6-amino-2-butoxy-9-{3-[(3-hydroxypropyl)amino]propyl}-7,9-dihydro-8H-purin-8-one (described in WO2007/031726 Example 1 step (viii)) (0.5 g) in NMP, the product from step (i) (0.35 g) was added and the mixture stirred for 10 mins. Sodium triacetoxyborohydride (1.25 g) was then added and stirred at rt for 16 hrs. The reaction mixture was diluted with water and passed through a SCX column, eluted with MeCN/2% NH3 (aq), and solvent removed to give the crude product. The product was purified via RPHPLC to afford the subtitle compound as a solid; 1H NMR DMSO 67.14-7.20 (m, 4H), 6.40 (s, 2H), 4.12 (t, 2H), 3.67 (t, 2H), 3.51 (s, 2H), 3.47 (s, 2H), 3.39 (t, 2H), 2.36-2.44 (m, 4H), 1.78-1.86 (m, 2H), 1.52-1.65 (m, 4H), 1.32-1.41 (m, 2H), 0.90 (t, 3H) MS multimode (+) 487

Workup

  1. stirringstirred at rt for 16 hrs
  2. washeluted with MeCN/2% NH3 (aq), and solvent
  3. customremoved
  4. customto give the crude product
  5. customThe product was purified via RPHPLC

Sources & evidence

ORD record
ord-af3a463c9f484350abc77d1f03f04f65
Source dataset
uspto-grants-2014_11
Patent number
US08895570B2

Reaction notes

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