Triethylamine → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid fluoride

HRID 871875Notes

Reaction equation

HRID 871875 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([OH:13])([CH3:12])[CH3:11])[C:5]([C:14]([OH:16])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.N1C(F)=NC(F)=NC=1[F:26]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([OH:13])([CH3:12])[CH3:11])[C:5]([C:14]([F:26])=[O:16])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12664Cyanuric fluorideHCID 866731432-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 891066152-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid fluorideYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 12.64 g (51.45 mmol) of the acid prepared in step 17.1 and 7.89 mL (56.60 mmol) of triethylamine in 250 mL of dichloromethane are added 6.51 mL (77.18 mmol) of cyanuric fluoride. The mixture is stirred at room temperature overnight and the solution is diluted with 590 mL of CH2Cl2 and 190 mL of ice-cold aqueous NaHCO3. The organic phase is washed twice with 250 mL of ice-cold aqueous NaHCO3 and dried over MgSO4. The solvent is then evaporated off under reduced pressure. 12.3 g of the expected product are obtained in the form of a yellow oil that solidifies slowly, and which is used as obtained in the following step. Yield=96%.

Workup

  1. washThe organic phase is washed twice with 250 mL of ice-cold aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record
ord-c1e7504816b04ea6a5e095e0a6f2a2cd
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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