Hydrochloric Acid → HCID 178455691, compound

HRID 591226Notes

Reaction equation

HRID 591226 reaction equation
[Na].[NH2:2][C:3]1[N:8]([NH2:9])[C:7](=[O:10])[CH:6]=[C:5]([CH3:11])[N:4]=1.[F:12][C:13]([F:21])([CH2:19][CH3:20])[C:14](OCC)=O.Cl>O1CCOCC1.C(O)C>[F:12][C:13]([C:14]1[N:2]=[C:3]2[N:4]=[C:5]([CH3:11])[CH:6]=[C:7]([OH:10])[N:8]2[N:9]=1)([F:21])[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9131753-Amino-2-imino-6-methyl-2,3-dihydropyrimidin-4(1H)-oneHCID 5360545SodiumHCID 22749276Ethyl 2,2-difluorobutanoate

Product 1

HCID 178455691HCID 178455691, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of NaEtO prepared from sodium (FLUKA, 0.152 g, 6.62 mmol) and ethanol (25 mL), Intermediate 1 (0.773 g, 5.52 mmol) was added, and the mixture was heated at 80° C. for 30 min. Then, the reaction was cooled down to room temperature and ethyl 2,2-difluorobutanoate (FLUOROCHEM, 1007 mg, 6.62 mmol) was added and the reaction mixture was stirred at 80° C. for 3 h. A solution of HCl (1.655 mL, 6.62 mmol) in dioxane was added and a white solid was formed. The residue was purified (silica gel column, eluting with DCM:MeOH mixtures from 100:0 to 90:10%) to obtain Intermediate 6 as a white solid.

Workup

  1. additionwas added
  2. temperatureThen, the reaction was cooled down to room temperature
  3. customa white solid was formed
  4. customThe residue was purified
  5. wash(silica gel column, eluting with DCM:MeOH mixtures from 100:0 to 90:10%)

Sources & evidence

ORD record
ord-083555a2301a4b0ab0362f0529b3cc77
Source dataset
uspto-grants-2016_01
Patent number
US09238653B2

Reaction notes

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