Triethylamine → 4-(5-Bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol

HRID 1182065Notes

Reaction equation

HRID 1182065 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[SH:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22]>C(#N)C>[Br:1][C:2]1[C:3]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 5482614-Sulfanylbutan-1-ol

Product 1

HCID 589818994-(5-Bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.27 g (10.0 mmol) of 5-bromo-2,4-dichloro-pyrimidine in 30 ml of acetonitrile is mixed while being stirred at −20° C. with 1.39 ml (10 mmol) of triethylamine. Then, a solution of 1.06 g (10 mmol) of 4-mercapto-1-butanol in 1 ml of acetonitrile is added in drops. The reaction mixture is heated overnight to room temperature while being stirred. The batch is filtered, and the filtrate is evaporated to the dry state. The residue that is obtained is purified by chromatography (Flashmaster II, hexane/ethyl acetate 1:1). 2.89 g (9.7 mmol, 97% of theory) of the product 4-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-butan-1-ol is obtained.

Workup

  1. temperatureThe reaction mixture is heated overnight to room temperature
  2. filtrationThe batch is filtered
  3. customthe filtrate is evaporated to the dry state
  4. customThe residue that is obtained
  5. customis purified by chromatography (Flashmaster II, hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-15557f5702e0467eabb7de0356413252
Source dataset
uspto-grants-2007_10
Patent number
US07288547B2

Reaction notes

Loading…