Sodium Bicarbonate → 3-(5-Isopropyl-2,6-dioxo-3-pyridin-4-ylmethyl-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

HRID 426218Notes

Reaction equation

HRID 426218 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:28]=[C:29]([CH3:31])[CH:30]=1)[O:9][C:10]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[C:14](=[O:23])[NH:13][C:12](=[O:24])[C:11]=1[CH:25]([CH3:27])[CH3:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O.CC(C)=O>[CH:25]([C:11]1[C:12](=[O:24])[NH:13][C:14](=[O:23])[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[C:10]=1[O:9][C:8]1[CH:7]=[C:6]([CH:30]=[C:29]([CH3:31])[CH:28]=1)[CH:2]=[O:1])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 591847936-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1-pyridin-4-ylmethyl-1H-pyrimidine-2,4-dione

Product 1

HCID 591847963-(5-Isopropyl-2,6-dioxo-3-pyridin-4-ylmethyl-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehydeYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1-pyridin-4-ylmethyl-1H-pyrimidine-2,4-dione (1.2 g, 2.83 mmol), p-toluenesulfonic acid monohydrate (538 mg, 2.83 mmol), and water (15 drops) in acetone (20 ml) was heated under reflux for 3 hr. After cooling to room temperature, excess sodium bicarbonate was added and the mixture was stirred for 1 hr. Then the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (9:1)) to afford 978 mg (91%) of 3-(5-Isopropyl-2,6-dioxo-3-pyridin-4-ylmethyl-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehyde as a white solid. 1H NMR (200 MHz, CDCl3) δ 1.12 (6H, d, J=7.0 Hz), 2.40 (3H, s), 2.70 (1H, m), 4.92 (2H, s), 6.90 (1H, s), 7.08 (1H, s), 7.11 (1H, s), 7.14 (1H, s), 7.43 (1H, s), 8.50 (2H, d, J=6.2 Hz), 9.73 (1H, s), 9.91 (1H, s). 6.85-6.89 (3H, m), 7.09 (1H, s), 7.21-7.27 (2H, m), 7.40 (1H, s), 8.98 (1H, s), 9.89 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. customThen the mixture was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent, EA:hexane (9:1))

Sources & evidence

ORD record
ord-e675922229bd4e8db7e49094461c6b64
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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