Triethylamine → (R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-ol

HRID 38213

Reaction equation

HRID 38213 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([I:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:17][C@H:18]([CH3:21])[CH2:19][OH:20]>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C@H:18]([CH3:21])[CH2:19][OH:20])[C:5]([I:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 2634382,4-Dichloro-5-iodopyrimidine

Product 1

HCID 59550865(R)-2-(2-chloro-5-iodopyrimidine-4-ylamino)propan-1-olYield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloro-5-iodopyrimidine (3.0 g; 10.9 mol) in acetonitrile (35 mL) was added triethylamine (1.32 g, 1.82 mL, 13.1 mmol), followed by (R)-2-aminopropanol (0.88 g, 11.8 mmol). The mixture was stirred at room temperature for 24 h and was then diluted with ethyl acetate, followed by extraction with brine, 10% aqueous citric acid, and aqueous sodium bicarbonate. After drying over sodium sulfate, the solvent was evaporated and the residue was purified by column chromatography to give the title compound (3.0 g, 88% yield).

Workup

  1. extractionfollowed by extraction with brine, 10% aqueous citric acid, and aqueous sodium bicarbonate
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6bcc1139f9224011bd5c597b37e59a37
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Linked notes

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