Potassium Carbonate → 2-(Cyclopentylmethyl)-4-[(3-fluorophenyl)amino]-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile

HRID 1724648Notes

Reaction equation

HRID 1724648 reaction equation
[C:1]([C:3](=[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)SC)[C:4]([O:6]C)=O)#[N:2].Cl.[CH:20]1([CH2:25][C:26]([NH2:28])=[NH:27])[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:20]1([CH2:25][C:26]2[NH:28][C:4](=[O:6])[C:3]([C:1]#[N:2])=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[N:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 689380642-Cyclopentylethanimidamide hydrochlorideHCID 68938107Methyl 2-cyano-3-[(3-fluorophenyl)amino]-3-(methylsulfanyl)-2-propenoate

Product 1

HCID 1360559412-(Cyclopentylmethyl)-4-[(3-fluorophenyl)amino]-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.1 g (0.37 mmol) of methyl 2-cyano-3-[(3-fluorophenyl)amino]-3-(methylsulfanyl)-2-propenoate and 0.06 g (0.41 mmol) of 2-cyclopentylethanamidine hydrochloride are dissolved in 1 ml of DMF and heated with 0.11 g (0.82 mmol) of potassium carbonate at 90° C. overnight. After filtration, the solvent is removed in vacuo and the residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B) purified. 70 mg (59% of theory) of the product are obtained as a colorless solid.

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed in vacuo
  3. customthe residue is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  4. custompurified
  5. custom70 mg (59% of theory) of the product are obtained as a colorless solid

Sources & evidence

ORD record
ord-49261121f87144d999ada48ce7ad5b2f
Source dataset
uspto-grants-2009_02
Patent number
US07488733B2

Reaction notes

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