Triethylamine → HCID 14814216, compound

HRID 1089258Notes

Reaction equation

HRID 1089258 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.[CH3:15][O:16][C:17]1[CH:40]=[CH:39][C:20]([CH2:21][O:22][CH2:23][CH:24]([O:37][NH2:38])[CH2:25][CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:19][CH:18]=1.C(N(CC)CC)C>O1CCOCC1>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22][CH2:23][CH:24]([O:37][NH:38][C:2]2[N:3]=[C:4]([NH:12][CH:13]=[O:14])[N:5]=[C:6]([Cl:11])[C:7]=2[NH:8][CH:9]=[O:10])[CH2:25][CH2:26][O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13989892N-(4,6-dichloro-2-formamido-pyrimidin-5-yl)formamideHCID 14814215HCID 14814215, compound

Product 1

HCID 14814216HCID 14814216, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4,6-dichloro-2,5-diformamidopyrimidine (3.27 g, 13.9 mmol), 1,4-bis(4-methoxybenzyloxy)but-2-oxyamine (5.06 g, 14 mmol) and triethylamine (5.88 ml, 42 mmol) in dioxan (100 ml) was heated at 100° C. for 90 minutes. The solution was allowed to cool, filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1) to afford 6-[1,4-bis (4-methoxybenzyloxy)but-2-oxyamino]-4-chloro-2,5-diformamidopyrimidine as a pale yellow foam. 1H NMR: δH (CDCl3) 1.88 (2H, m, 3-H), 3.54 (4H, m, 1'-H and 4'-H), 3.73 (3H, s, CH3), 3.74 (3H, s, CH3), 4.07 (1H, m, 2'-H), 4.37 (4H, m, 2×ArCH2), 6.88 (4H, m, ArH), 7.21 (4H, m, ArH), 9.17, 9.27, 9.30, 9.43 (total 2H, 4×s, D2O exchange leaves s at 9.27, 2×HCO), 10.67 (1H, br.s, D2O exchangeable, NH) and 10.85 (1H, br.s, D2O exchangeable, NH).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customthe solvent removed
  4. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-b9d2f983b6094ebd9684079672ea0936
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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