Diisopropylethylamine → (S)-2-{4-[4-(1-Acetylamino-ethyl)-phenyl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](Cl)=[N:9][CH:10]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:27]([NH:26][C@H:24]([C:21]1[CH:22]=[CH:23][C:18]([CH:15]2[CH2:14][CH2:13][N:12]([C:8]3[N:7]=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:10][N:9]=3)[CH2:17][CH2:16]2)=[CH:19][CH:20]=1)[CH3:25])(=[O:29])[CH3:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 1.52 g (8.5 mmol) 2-chloropyrimidine-5-carboxylic acid methyl ester in 80 mL NMP are added 2.1 g (8.5 mmol (S)—N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) and 2.9 mL (17.1 mmol) DIPEA and the mixture is stirred for 4 h at 100° C. The solvent is removed in vacuo. The residue is treated with 100 mL MeOH and 10 mL 4N sodium hydroxide solution is added. The mixture is stirred for 1 h at 60° C. After cooling to rt 4N HCl solution is added until the pH is acidic. The precipitate is collected and dried to yield the desired product.
Workup
- customThe solvent is removed in vacuo
- additionThe residue is treated with 100 mL MeOH and 10 mL 4N sodium hydroxide solution
- additionis added
- stirringThe mixture is stirred for 1 h at 60° C
- temperatureAfter cooling to rt 4N HCl solution
- additionis added until the pH
- customThe precipitate is collected
- customdried
Sources & evidence
- ORD record
- ord-0016a09d847c4769af0ad2bf9bc1ac8c
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006450B2
Reaction notes
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