Water → HCID 68679889, compound

HRID 1989084Notes

Reaction equation

HRID 1989084 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].C(O[C:19]([C:21]1[C:22](Cl)=[N:23][C:24]([S:27][CH3:28])=N[CH:26]=1)=[O:20])C.[CH2:30](N(CC)CC)[CH3:31].[OH2:37].[CH2:38](Cl)Cl>>[CH2:30]([O:37][C:19]([C:21]1[C:26]([N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[CH:38][C:24]([S:27][CH3:28])=[N:23][CH:22]=1)=[O:20])[CH3:31]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 90196N-(Phenylmethyl)-beta-alanine ethyl ester

Product 1

HCID 68679889HCID 68679889, compound

Procedure

3-Benzylamino-propionic acid ethyl ester (2.0 g, 9.6 mmol) and 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (2.2 g, 9.6 mmol) were combined in DCM (50 mL) and triethylamine (1.5 g, 14.5 mmol) was added. After 14 h, water (25 mL) was added and the organic layer was separated, dried (MgSO4), and concentrated. Chromatography on silica (0-30% EtOAc/hexanes gradient) provided 2.91 g of 4-[benzyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyridine-5-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.46 (s, 1H), 7.23-7.33 (m, 5H), 4.75 (s, 2H), 4.21 (q, 2H, J=7.2 Hz), 4.06-4.15 (m, 2H), 3.77 (t, 2H, J=7.2 Hz), 2.66-2.70 (app t, 2H), 2.45 (s, 3H), 1.19-1.29 (m, 6H).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4225be0e788a4c6bb97f7c62243a9435
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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