Acetic Acid → HCID 69085270, compound

HRID 1374869Notes

Reaction equation

HRID 1374869 reaction equation
[NH2:1][C@@H:2]([C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=[O:19])[C:9]([CH3:20])=[C:8]([CH3:21])[N:7]=1)[CH:3]([CH3:5])[CH3:4].[CH:22]1[N:23](CC=O)[CH:24]=[C:25]2[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]2.[C:34]([OH:37])(=O)[CH3:35].C(O[BH-](OC(=O)C)OC(=O)C)(=[O:40])C.[Na+]>ClC(Cl)C.CCOC(C)=O.CCCCCC>[CH2:12]([N:11]1[C:10](=[O:19])[C:9]([CH3:20])=[C:8]([CH3:21])[N:7]=[C:6]1[C@H:2]([NH:1][CH2:30][CH2:22][N:23]1[C:34](=[O:37])[C:35]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:40])[CH:3]([CH3:4])[CH3:5])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 69018345HCID 69018345, compoundHCID 86591905HCID 86591905, compound

Product 1

HCID 69085270HCID 69085270, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-((R)-1-Amino-2-methyl-propyl)-3-benzyl-5,6-dimethyl-3-H-pyrimidin-4-one (0.500 g, 1.75 mMol) and 2H-isoindole-2-acetaldehyde [2913-97-5] (0.661 g 3.50 mMol) were dissolved in dichloroethane (20 mL). Glacial acetic acid was added (0.400 mL, 0.70 mMol) followed by sodium triacetoxy borohydride (0.942 g, 4.40 mMol). The reaction stirred at room temperature under nitrogen for 3.5 h. The reaction was quenched with NaHCO3 (sat. Aq.) and extracted with EtOAc (3×). The organic layer was evaporated under reduced pressure and purified by flash chromatography. (EtOAc/hexane 50–95% gradient) to give the title compound 420 mg (0.92 mMol) MS (ES) m/e 459 (M+H)+.

Workup

  1. customThe reaction was quenched with NaHCO3 (sat. Aq.)
  2. extractionextracted with EtOAc (3×)
  3. customThe organic layer was evaporated under reduced pressure
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-eba06cd966124328917c851c566b65c0
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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