Formamide → 5-propan-2-yl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-one

HRID 529151Notes

Reaction equation

HRID 529151 reaction equation
[NH2:1][C:2]1[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[C:3]=1[C:10]([O:12]C)=O.C([O-])=O.[NH4+].[CH:18]([NH2:20])=O>O>[CH:7]([CH:4]1[C:3]2[C:10]([OH:12])=[N:20][CH:18]=[N:1][C:2]=2[CH2:6][CH2:5]1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 68735644Methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate

Product 1

HCID 1784388195-propan-2-yl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-4-oneYield 134.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 2-amino-5-isopropylcyclopent-1-enecarboxylate (3.272 g, 17.86 mmol), ammonium formate (5.630 g, 89.28 mmol), and formamide (7.092 mL, 178.6 mmol) was heated at 150° C. for 20 hours. The reaction was diluted with water, and extracted with 1:5 IPA:DCM, until no more product in aqueous by TLC. The combined organics were concentrated under reduced pressure, dissolved in DCM and dried Na2SO4. The reaction was filtered and concentrated to give 5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol (4.29 g, 100%), which was used without further purification. LCMS (APCI+) m/z 179.0 [M+H]+; Rt=2.33 min.

Workup

  1. extractionextracted with 1:5 IPA
  2. concentrationThe combined organics were concentrated under reduced pressure
  3. dissolutiondissolved in DCM
  4. filtrationThe reaction was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c57352dffa945a3a156f1a2f11ff8c6
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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