Methylamine → HCID 58739054, compound

HRID 720291Notes

Reaction equation

HRID 720291 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[CH:26]([N:29](CC)C(C)C)(C)C.CN>C(#N)C.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:29][CH3:26])[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 21060065HCID 21060065, compound

Product 1

HCID 58739054HCID 58739054, compoundYield 303.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methanesulfonyl-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (1.180 g, 3.22 mmol) in acetonitrile (20 ml) was treated at 25° C. with N,N-diisopropylethylamine (1.5 ml, 0.87 mmol) followed by 4.8 ml (9.6 mmol) of a 2M solution of methylamine in tetrahydrofuran. After 30 min, the solvent was evaporated in vacuo and the residue was chromatographed on silica gel (elution toluene-ethyl acetate, 25:75) to give 0.838 g (82% yield) of the title ester as a clear syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.30 (3H, t, J=7.1 Hz, CH3), 3.04 (3H, d, J=5.1 Hz, NCH3), 3.42 (3H, s, NCH3), 4.32 (2H, q, J=7.1 Hz, OCH2), 4.58 (1H, broad q, NH), 5.07 (2H, s, OCH2), 7.3–7.37 (3H, m, aromatics), 7.47 (2H, m, aromatics). HRMS (FAB POS) calculated for C16H20N3O4 [M+H+]: 318.145381. found: 318.144860.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel (elution toluene-ethyl acetate, 25:75)

Sources & evidence

ORD record
ord-e182e757a6c04524ae2fd1ddb4314f4f
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

Loading…