Triethylamine → HCID 22476537, compound

HRID 2184374Notes

Reaction equation

HRID 2184374 reaction equation
[C:1]([O:5][C:6]([N:8]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:9]1[N:14]=[C:13]([C:15](OC)=[O:16])[CH:12]=[C:11]([N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C>O1CCCC1.CN(C1C=CC=CN=1)C>[C:37]([O:36][C:34]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[C:11]([N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[N:10]=1)=[O:35])([CH3:38])([CH3:39])[CH3:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 17951912HCID 17951912, compound

Product 1

HCID 22476537HCID 22476537, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2,6-di(bis(tert-butoxycarbonyl)amino)pyrimidine-4-carboxylate Crude methyl 2,6-diaminopyrimidine-4-carboxylate (2.52 g, 15 mmol) was suspended in dry tetrahydrofuran (200 ml) then treated sequentially with di-tert-butyl dicarbonate (19.6 g, 90 mmol), triethylamine (16.7 ml, 120 mmol), and 4 dimethylaminopyridine (0.092 g, 0.75 mmol). This mixture was refluxed gently for 16 h, evaporated, dissolved in diethyl ether, washed with water and brine, dried and evaporated to give a dark red gum. This residue was purified by flash chromatography, eluting with 0-18% ethyl acetate in petroleum ether, to give the title compound as an off-white foam (4.58 g, 54%); m/z (APCI+) 569 [MH]+100%.

Workup

  1. temperatureThis mixture was refluxed gently for 16 h
  2. customevaporated
  3. dissolutiondissolved in diethyl ether
  4. washwashed with water and brine
  5. customdried
  6. customevaporated
  7. customto give a dark red gum
  8. customThis residue was purified by flash chromatography
  9. washeluting with 0-18% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-08bc1b8fc60a4e10a157eb003a7cd354
Source dataset
uspto-grants-2005_05
Patent number
US06900345B2

Reaction notes

Loading…