3-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acid → 3-(2-Methyl-pyrimidin-5-yl)-10-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-decanoic acid

HRID 2120708Notes

Reaction equation

HRID 2120708 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]2[NH:26][CH2:25][CH2:24][CH2:23][N:22]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 234355223-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 99470463-(2-Methyl-pyrimidin-5-yl)-10-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-decanoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 24-9 (47 mg, 0.131 mmol) in ethanol (1 mL) was treated with 10% palladium on carbon (7 mg) and hydrogen gas at one atmosphere (6 days). The reaction mixture was filtered through celite and the filtrate evaporated in vacuo. PCTLC (SiO2, 1 mm, 2% AcOH; 18% MeOH; 80% CHCl3) afforded 24-10 (37 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-efa5a9a724794267b36be96eae85b931
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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