4-Toluenesulfonyl chloride → HCID 59823038, compound

HRID 1660873Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=2[N:5]([CH3:14])[C:4](=[O:15])[CH:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:1][C:2]2[C:11]3[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[N:7][C:6]=3[N:5]([CH3:14])[C:4](=[O:15])[CH:3]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-hydroxy-3,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (compound 1C, 125 mg, 0.60 mmol, 1 eq), p-toluenesulfonyl chloride (138 mg, 0.72 mmol, 1.2 eq) and triethylamine (126 μl, 0.90 mmol, 1.5 eq) were dissolved in acetonitrile (2 ml). The mixture was heated at reflux (oil bath at 110° C.) for 3 hours to yield 3,8-dimethyl-4,7-dioxo-3,4,7,8-tetrahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzenesulfonate (compound 1D). The product was confirm by LC-MS. Solvent was removed in vacuo and the crude product 3,8-dimethyl-4,7-dioxo-3,4,7,8-tetrahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzenesulfonate used in the following reaction.

Workup

temperatureThe mixture was heated

Sources & evidence

ORD record: ord-b82ea04d4723480fb093b09dfa4a18c4
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030317B2

Reaction notes

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