4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → 4-[Cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

HRID 1989017Notes

Reaction equation

HRID 1989017 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH3:2].[CH2:15]([O:17][C:18]([C:20]1[C:21](Cl)=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:15]([O:17][C:18]([C:20]1[C:21]([N:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 243063Ethyl 3-(cyclohexylamino)propanoate

Product 1

HCID 685834964-[Cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyclohexylamino-propionic acid ethyl ester (1.0 g, 5.0 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.17 g, 5.02 mmol) were combined in DCM (15 mL) and diisopropylethylamine (0.81 g, 6.3 mmol) was added. After 16 h, the solution was partitioned between water and DCM and the organic layer was dried (MgSO4) and concentrated. Chromatography (0-20% EtOAc/hexanes gradient) provided 1.63 g (84%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.39 (s, 1H) 5.30 (s, 1H), 4.30 (q, 2H, J=7.1 Hz), 4.14 (q, 1H, J=7.1 Hz), 3.76-3.80 (m, 2H), 2.65-2.69 (m, 2H), 2.49 (s, 3H), 1.81-1.84 (m, 2H), 1.34-1.40 (m, 7H), 1.12-1.27 (m, 7H).

Workup

  1. customthe solution was partitioned between water and DCM
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-885d4f060d6e4008ad5740447204df58
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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