Pyridine → N3-benzoylthymine

HRID 1477172Notes

Reaction equation

HRID 1477172 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].N1C=CC=CC=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[C:16]([N:4]1[C:5](=[O:6])[C:7]([CH3:8])=[CH:9][NH:1][C:2]1=[O:3])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1135ThymineHCID 7412Benzoyl chloride

Product 1

HCID 10933275N3-benzoylthymine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of thymine (1) in THF was added pyridine and the reaction was cooled to 0° C. Benzoyl chloride was added carefully at 0° C. and the reaction was stirred overnight at room temperature. The reaction mass was evaporated to give the crude solid which was purified by SiO2 flash chromatography to give the N3-benzoyl thymine (4) as a white solid. NMR (600 MHz, CD3OD): δ 7.94 (m, 2H), 7.71 (t, 1H, J=7.3 Hz), 7.57 (m, 2H), 7.38 (s, 1H), 1.90 (s, 3H); Mass (ESI-MS): 231.22 (M+H); m.p: 178-180° C.

Workup

  1. customThe reaction mass was evaporated
  2. customto give the crude solid which
  3. customwas purified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-26215334e2f64badafdba3b74534587f
Source dataset
uspto-grants-2016_08
Patent number
US09403778B2

Reaction notes

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