Formamide → HCID 178435582, compound
Reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][CH:4]([CH2:7][CH3:8])[C:3]=1[C:9]([O:11]C)=O.C([O-])=O.[NH4+].[CH:17]([NH2:19])=O>>[CH2:7]([CH:4]1[C:3]2[C:9]([OH:11])=[N:19][CH:17]=[N:1][C:2]=2[CH2:6][CH2:5]1)[CH3:8]Participants
Conditions
- Temperature
- 150 °C
Procedure
Methyl 2-amino-5-ethylcyclopent-1-enecarboxylate (1.62 g, 9.57 mmol) was combined with ammonium formate (3.02 g, 47.9 mmol) and formamide (3.80 mL, 95.7 mmol), and the reaction mixture was heated to 150° C. for 16 hours. Conversion was confirmed by LCMS. The reaction was cooled to room temperature and partitioned between a 5:1 DCM/i-PrOH solution and water. The aqueous layer was extracted multiple times with the same DCM/i-PrOH solution. The combined extracts were concentrated to dryness and partitioned between DCM and brine. The organic portion was concentrated to provide 5-ethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (1.13 g, 6.88 mmol, 71.9% yield) as an oil, which was taken to the next step without purification. MS (APCI+) [M+H]: 165.0.
Workup
- temperatureThe reaction was cooled to room temperature
- custompartitioned between a 5:1 DCM/i-PrOH solution and water
- extractionThe aqueous layer was extracted multiple times with the same DCM/i-PrOH solution
- concentrationThe combined extracts were concentrated to dryness
- custompartitioned between DCM and brine
- concentrationThe organic portion was concentrated
Sources & evidence
- ORD record
- ord-1273ef0a875744629825a09627858978
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346805B2
Reaction notes
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