Sodium Hydroxide → 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid

HRID 2381390Notes

Reaction equation

HRID 2381390 reaction equation
C[O:2][C:3](=[O:27])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[N:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[N:20]=[C:21]([CH3:26])[CH:22]=[C:23]([CH3:25])[N:24]=3)[CH:13]=[N:12]2)[C:3]([OH:27])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668750953-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

Product 1

HCID 579191953-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acidYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (206 mg, 0.55 mmol) in tetrahydrofuran (4 mL) was treated with a 4N aqueous sodium hydroxide solution (0.17 mL) and was stirred at 25° C. for 4 h. The reaction was partitioned between water (3 mL) and ether. The aqueous layer was back extracted with ether. The aqueous layer was then acidified to pH 3-4 with a 1N aqueous hydrochloric acid solution. The resulting precipitate was filtered, rinsed with water (1 mL), and dried in vacuo to afford 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (40 mg, 20%); LC-MS: tR=3.71 min, 359 [M+H]+. HPLC: tR=7.02 min, 96.21% at 214 nm, 98.34% at 254 nm. 1H NMR (300 MHz, DMSO-d6): δ13.03 (broad, 1H), 8.12 (d, 1H, J=2.7 Hz), 7.19 (s, 1H), 6.85 (d, 1H, J=2.4 Hz), 5.36 (dd, 1H, J=10.5 Hz, J=4.2 Hz), 2.41 (s, 6H), 2.24-2.14 (m, 1H), 2.05-1.97 (m, 1H), 1.71-1.44 (m, 7H), 1.17-1.04 (m, 2H).

Workup

  1. customThe reaction was partitioned between water (3 mL) and ether
  2. extractionThe aqueous layer was back extracted with ether
  3. filtrationThe resulting precipitate was filtered
  4. washrinsed with water (1 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4ac8552bea3041bc895ccc3ccab10a3e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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