Triethylamine → HCID 13989893, compound

HRID 1089247Notes

Reaction equation

HRID 1089247 reaction equation
Cl[C:2]1[C:7]([NH:8][CH:9]=[O:10])=[C:6]([Cl:11])[N:5]=[C:4]([NH:12][CH:13]=[O:14])[N:3]=1.[CH2:15]([O:22][CH2:23][CH2:24][CH2:25][O:26][NH2:27])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[CH2:15]([O:22][CH2:23][CH2:24][CH2:25][O:26][NH:27][C:2]1[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=[C:6]([Cl:11])[C:7]=1[NH:8][CH:9]=[O:10])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13989887O-[3-(Benzyloxy)propyl]hydroxylamineHCID 13989892N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamide

Product 1

HCID 13989893HCID 13989893, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (5.4 g, 23.0 mmol), 3-benzyloxyprop-1-oxyamine (4.14, 23.0 mmol), triethylamine (10 ml) and dioxan (50 ml) was stirred at reflux temperature for 3 hours, cooled, filtered and evaporated to dryness. Column chromatography on silica gel (eluted with chloroform-ethanol, 25:1) gave the title compound (4.38 g, 50%). IR: υmax (KBr) 3248, 1692, 1589, 1570, 1473, 1420 cm-1. 1H NMR: δH [(CD3)2SO] 1.88 (2H, quintet, J=6.3 Hz, CH2CH2CH2) 3.57 (2H, t, J=6.3 Hz, CH2OCH2Ph), 3.95 (2H, t, 6.3 Hz, CH2ONH), 4.47 (2H, s, CH2Ph), 7.32 (5H, m, Ph), 8.14 (1H, s, CHONH), 9.26 (1H, s, CHONH), 9.42 (1H, br.s, D2O exchangeable, NHOCH2), 10.83 (2H, br.s, 2×NHCHO).

Workup

  1. temperatureat reflux temperature for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-333967a71c8b4187958a03cca019a60e
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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