Triethylamine → HCID 50898356, compound

HRID 1880196Notes

Reaction equation

HRID 1880196 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:23]>ClCCl>[CH3:27][C:26]([CH3:29])([CH3:28])[CH2:25][O:24][C:22]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]1=[O:8])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33521852,2-Dimethylpropyl carbonochloridateHCID 178484257HCID 178484257, compound

Product 1

HCID 50898356HCID 50898356, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an 8 mL screw-cap vial was added dichloromethane (CH2Cl2; 3 milliliters (mL)), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 milligrams (mg), 0.54 millimole (mmol)), triethylamine (Et3N; 120 mg, 1.18 mmol), and 2,2-dimethylpropyl chloroformate (90 mg, 0.60 mmol). After shaking for 1.5 hours (h) at room temperature, the mixture was partitioned between ethyl acetate (EtOAc) and water (H2O). The organic phase was dried over magnesium sulfate (MgSO4), filtered, and evaporated. The crude material was purified by reverse phase chromatography to yield 4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylic acid 2,2-dimethyl-propyl ester as a white solid (33 mg, 20%): mp 162-164° C.; 1H NMR (300 MHz, CDCl3) δ 8.77 (s, 1H), 7.93 (d, J=6.6 Hz, 1H), 4.08 (s, 2H), 3.27 (s, 3H), 3.20 (s, 3H), 1.05 (s, 9H); ESIMS m/z 299 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. customthe mixture was partitioned between ethyl acetate (EtOAc) and water (H2O)
  3. dry with materialThe organic phase was dried over magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-dc326d962ec74853a71e4125c8cfacfb
Source dataset
uspto-grants-2012_11
Patent number
US08318758B2

Reaction notes

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