Hydrochloric Acid → HCID 18507587, compound

HRID 1356019Notes

Reaction equation

HRID 1356019 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)=[N:8][C:9]([NH2:14])=[N:10][C:11]=1[S:12][CH3:13])=[CH2:5])C.Cl>C1COCC1>[NH2:14][C:9]1[N:8]=[C:7]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[C:6]([C:4](=[O:3])[CH3:5])=[C:11]([S:12][CH3:13])[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18507295HCID 18507295, compound

Product 1

HCID 18507587HCID 18507587, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 670 mg (2,42 mmol) 5-(1-ethoxy-vinyl)-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine in 18 ml THF was added 2.00 ml (2.00 mmol) 1M hydrochloric acid and stirring continued for 43 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and sodium bicarbonate solution and the layers separated. The organic phase was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was triturated in ethyl acetate/ether to afford 200 mg (33%) 1-(2-amino-4-furan-2-yl-6-methylsulfanyl-pyrimidin-5-yl)-ethanone as a light brown crystalline solid. EI-MS m/e (%): 249 (M+, 14), 234 (38), 221 (100), 206 (20), 43 (30).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium bicarbonate solution
  2. customthe layers separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in ethyl acetate/ether

Sources & evidence

ORD record
ord-6ef02595a5614b10b434fc4aa6513b97
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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