Hydrochloric Acid → 3-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acid

HRID 860099Notes

Reaction equation

HRID 860099 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH:6]([C:21]1[CH:22]=[N:23][C:24]([CH3:27])=[N:25][CH:26]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)C.[OH-].[Na+].Cl>O1CCOCC1>[CH3:27][C:24]1[N:25]=[CH:26][C:21]([CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]2[N:16]=[CH:17][CH:18]=[CH:19][N:20]=2)[CH2:5][C:4]([OH:28])=[O:3])=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 206224843-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acid ethyl ester

Product 1

HCID 234355223-(2-Methyl-pyrimidin-5-yl)-10-(pyrimidin-2-ylamino)-decanoic acidYield 57.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 24-8 (170 mg, 0.441 mmol) in 1,4-dioxane (2 mL) was treated with 1M aqueous NaOH (1.50 mL) at room temperature (90 min). The reaction was neutralized with 1M aqueous HCl (1.50 mL) and the solvents were removed in vacuo. PCTLC (SiO2, 2 mm, 10% MeOH; 25% EtOAc, 65% CHCl3) afforded 24-9 (90 mg).

Workup

  1. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f60027cc6da5498ba258f9693a1046f4
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

Loading…