Triethylamine → Thymine

HRID 2303754Notes

Reaction equation

HRID 2303754 reaction equation
[N:1]1(CC(N2CCNCC2=O)=O)[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18461966HCID 18461966, compound

Product 1

HCID 1135ThymineYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5.5 g, of N-(thymin-1-ylacetyl)-piperazinone (20.6 mmol) was suspended in 200 mL of dry DCM and treated with 3.77 g (1.5 eq, 30.9 mmol) DMAP, 11.23 g (51.5 mmol, 2.5 eq) Boc-anhydride and 7.2 mL (51.5 mmol, 2.5 eq) of triethylamine. The reaction also results in protection of the secondary amino group on the thymine. The reaction mixture was stirred at room temperature for 3-4 hours, while following the reaction progress by TLC. Upon completion, the reaction mixture was concentrated by rotary evaporation, and the resulting oil was resuspended in DCM. The organic phase was washed successively with 0.1 N HCl solution (2×25 mL), water (2×100 mL) and dried over sodium sulfate. Concentration and purification by recrystallization from diethyl ether afforded 6 g of the Boc-protected thymine PNA precursor (80% yield) as a white solid.

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-8b6e3b1231dd43fc8c0f7205e0d76d01
Source dataset
uspto-grants-2002_08
Patent number
US06433134B1

Reaction notes

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