Hydrochloric Acid → HCID 68583787, compound

HRID 1989018Notes

Reaction equation

[Na].C(O[C:5]([C:7]1[C:8]([N:15]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1)=[O:6])C.CC(C)([O-])C.[Na+].Cl>C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:21]([O:20][C:18]([CH:17]1[CH2:16][N:15]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:8]2[N:9]=[C:10]([S:13][CH3:14])[N:11]=[CH:12][C:7]=2[C:5]1=[O:6])=[O:19])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium (25 wt % dispersion in paraffin wax, 0.10 g, 3.8 mmol) was added to t-butanol (1.8 mL) at rt. After 10 minutes, a solution of 4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 2.5 mmol) in 10 mL of toluene was added to the sodium t-butoxide solution and the resulting mixture was heated at 90° C. for 30 minutes. The reaction mixture was then cooled and the solution was adjusted to pH 7 using a 1N HCl solution. The solution was then extracted with EtOAc (2×20 mL) and the organic layer was dried (MgSO4) and concentrated to provide 0.55 g, (42%) of the title compound. 1H NMR indicated the presence of both enol and keto forms in a 1:1.75 ratio. 1H-NMR (400 MHz, CDCl3) δ ppm 8.63 (s, 1H), 8.18 (s, 1H), 4.76-4.82 (m), 4.58-4.68 (m), 4.16-4.36 (m), 3.91-3.96 (m), 3.60-3.64 (m), 3.46-3.49 (m), 2.53 (s, 3H), 2.50 (s, 5.25H), 1.86-1.89 (m), 1.71-1.73 (m), 1.32-1.56 (m), 1.26 (t, J=7.2 Hz), 1.10-1.21 (m).

Workup

temperatureThe reaction mixture was then cooled
extractionThe solution was then extracted with EtOAc (2×20 mL)
dry with materialthe organic layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-44723f6227e345f1abf8f5696d866729
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642270B2

Reaction notes

Loading…