Triethylamine → 4-Ethylamino-2-methylthio-5-pyrimidinecarboxylic acid fluoride

HRID 871840Notes

Reaction equation

HRID 871840 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([C:10](O)=[O:11])=[CH:8][N:7]=[C:6]([S:13][CH3:14])[N:5]=1)[CH3:2].C(N(CC)CC)C.N1C(F)=NC(F)=NC=1[F:24]>C(Cl)Cl>[CH2:1]([NH:3][C:4]1[C:9]([C:10]([F:24])=[O:11])=[CH:8][N:7]=[C:6]([S:13][CH3:14])[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12664Cyanuric fluorideHCID 222201684-Ethylamino-2-methylthiopyrimidine-5-carboxylic acid

Product 1

HCID 891065744-Ethylamino-2-methylthio-5-pyrimidinecarboxylic acid fluorideYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 3.0 g (14.0 mmol) of 4-ethylamino-2-methylthio-5-pyrimidinecarboxylic acid and 2.1 mL (15.0 mmol) of triethylamine in 50 mL of CH2Cl2 are added 2.3 mL (28.0 mmol) of cyanuric fluoride. The mixture is stirred for 3 hours and the solution is diluted with 250 mL of CH2Cl2 and 75 mL of ice-cold water. After separation of the phases by settling, the organic phase is washed with 75 mL of ice-cold water and dried over MgSO4. The solvent is then evaporated off under reduced pressure. 3.0 g of expected product are obtained in the form of a greenish gum. The yield is quantitative.

Workup

  1. customAfter separation of the phases
  2. washthe organic phase is washed with 75 mL of ice-cold water
  3. dry with materialdried over MgSO4
  4. customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-10a3fe250faa47628fb912bf008234a6
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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