Ammonia → HCID 58739057, compound

HRID 720290Notes

Reaction equation

HRID 720290 reaction equation
[NH3:1].[CH2:2]([O:4][C:5]([C:7]1[N:8]=[C:9](S(C)(=O)=O)[N:10]([CH3:22])[C:11](=[O:21])[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6])[CH3:3]>C(#N)C>[CH2:2]([O:4][C:5]([C:7]1[N:8]=[C:9]([NH2:1])[N:10]([CH3:22])[C:11](=[O:21])[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21060065HCID 21060065, compound

Product 1

HCID 58739057HCID 58739057, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Gaseous ammonia was bubbled at 25° C. in a solution of 2-methanesulfonyl-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.200 g, 0.55 mmol) in acetonitrile (4 ml). After 30 min, the solvent was evaporated in vacuo and the residue was chromatographed on silica gel (elution toluene-ethyl acetate, 6:4 to 1:1) to give 0.099 g (59% yield) of the title ester as a white solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 1.19 (3H, t, J=7.1 Hz, CH3), 3.29 (3H, s, NCH3), 4.18 (2H, q, J=7.1 Hz, OCH2), 4.89 (2H, s, OCH2), 7.21 (2H, broad s, NH2), 7.31–7.37 (5H, m, aromatics). Anal. Calcd for C15H17N3O4: C 59.39; H, 5.64; N, 13.85. Found: C, 59.31; H, 5.46, N 13.72.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel (elution toluene-ethyl acetate, 6:4 to 1:1)

Sources & evidence

ORD record
ord-b27fa165f43f4a9da73cc257e745e0a0
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

Loading…