Acetic Acid → 3-(5-Acetoxy-6-bromohexyl)-1-methylthymine

HRID 361521Notes

Reaction equation

HRID 361521 reaction equation
[OH:1][CH:2]([CH2:17]O)[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16].[BrH:19].[C:20]([OH:23])(=O)[CH3:21].C(=O)(O)[O-].[Na+]>O.ClCCl.CC(C)=O>[C:20]([O:1][CH:2]([CH2:17][Br:19])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16])(=[O:23])[CH3:21]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 232879373-(5,6-Dihydroxyhexyl)-1-methylthymine

Product 1

HCID 232959113-(5-Acetoxy-6-bromohexyl)-1-methylthymineYield 100%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5,6-dihydroxyhexyl)-1-methylthymine (1.65 g, 6.4 mmol) and a 30% solution of hydrogen bromide in acetic acid (3.8 mL, 19.3 mmol) in water (5 mL) and acetone (10 mL) was stirred for 1.5 hours. The mixture was then added to a flask containing sodium bicarbonate (6.7 g), water (40 mL) and dichloromethane (50 mL). After 15 minutes of vigorous stirring, the layers were separated and the aqueous layer washed with dichloromethane (2×50 mL). The combined organic layers were dried over sodium sulfate. The solvent was evaporated under vacuum to yield 2.30 g (100%) of 3-(5-acetoxy-6-bromohexyl)-1-methylthymine as a yellow oil. The bromoacetate was used in the next step without further purification. A solution of 3-(5-acetoxy-6-bromohexyl)-1-methylthymine (2.30 g, 6.4 mmol) in methanol (10 mL) was treated with a 1M methanol solution of sodium methoxide (7 mL). After stirring for 15 minutes, the solution was poured into water (60 mL) and extracted with 20% ethanovdichloromethane (2×70 mL). The combined organic layers were dried over sodium sulfate and the solvent evaporated under vacuum to yield 1.30 g (85%) 3-(5,6-oxidohexyl)-1-methylthymine as a white solid.

Workup

  1. additionThe mixture was then added to a flask
  2. customthe layers were separated
  3. washthe aqueous layer washed with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-7174ceea197e46518d66db02afe26a1e
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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