Cyclopentylamine → Ethyl 4-(cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:27][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Commercially available 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (6) (25 g, 107 mmol) was dissolved in THF. Subsequently, triethylamine (32.6 g, 322 mmol) and cyclopentylamine (10 g, 117 mmol) were added to the reaction mixture. The combination was stirred over night at room temperature. Precipitated salts were filtered away from solvent and discarded. The collected solvent was then evaporated in vacuo to give an oil. The resultant oil was dissolved in ethyl acetate, washed with sodium bicarbonate, and then dried over Na2SO4. The drying aid was filtered away and the resultant solvent was evaporated under vacuum to give 23.3 g of product (7). 1H NMR (300 MHz, CDCl3), δ 8.60 (s, 1H), 8.25 (br s, 1H), 4.49-4.54 (m, 1H), 4.30 (q, 2H), 2.52 (s, 3H), 2.00-2.10 (m, 2H), 1.50-1.79 (m, 6H), 1.35 (t, 3H).
Workup
- filtrationPrecipitated salts were filtered away from solvent
- customThe collected solvent was then evaporated in vacuo
- customto give an oil
- washwashed with sodium bicarbonate
- dry with materialdried over Na2SO4
- filtrationThe drying aid was filtered away
- customthe resultant solvent was evaporated under vacuum
Sources & evidence
- ORD record
- ord-4ee6ddb18f0d46ee8524ce826c5f0f06
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987267B2
Reaction notes
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