Phenylacetaldehyde → HCID 57899189, compound

HRID 1470249Notes

Reaction equation

HRID 1470249 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[NH:10][C:11](=[O:17])[NH:12]3)[CH2:4][CH2:3]1.[C:18]1([CH2:24][CH:25]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClCCCl.CO>[CH2:25]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:16]=[CH:15][N:14]=[C:13]3[C:9]=2[NH:10][C:11](=[O:17])[NH:12]3)[CH2:4][CH2:3]1)[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11715612HCID 11715612, compound

Product 1

HCID 57899189HCID 57899189, compoundYield 10.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

A mixture of 6-(4-aminopiperidin-1-yl)-7,9-dihydropurin-8-one (Example 4B, 0.045 g, 0.20 mmol), phenylacetaldehyde (0.025 ml, 0.20 mmol), NaBH(OAc)3 (0.065 g, 0.30 mmol) and acetic acid (5 drops) in 1,2-dichloroethane (2 ml) and MeOH (0.5 ml) was stirred at room temperature for 2 hours. The solution was absorbed onto a 5 g SCX-II acidic resin cartridge and eluted with MeOH, then 1M NH3-MeOH. The basic eluant was concentrated. Preparative thin layer chromatography (t.l.c.), eluting with 1% NH3 (aq)/9% MeOH/90% CH2Cl2 gave the product as an off white solid (0.007 g, 10%). LC/MS: (LCT) Rt 3.62 [M+H]+339.

Workup

  1. customThe solution was absorbed onto a 5 g SCX-II acidic resin cartridge
  2. washeluted with MeOH
  3. concentrationThe basic eluant was concentrated
  4. washPreparative thin layer chromatography (t.l.c.), eluting with 1% NH3 (aq)/9% MeOH/90% CH2Cl2

Sources & evidence

ORD record
ord-61ff28f0806e451a967701f34d949f63
Source dataset
uspto-grants-2015_04
Patent number
US09006430B2

Reaction notes

Loading…