Triethylamine → 5-(2-Isocyanatopropan-2-yl)pyrimidine

HRID 2294942Notes

Reaction equation

HRID 2294942 reaction equation
C[C:2]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)([CH3:6])[C:3]([O-])=O.[Li+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.C([N:33]([CH2:36]C)CC)C>C(O)(C)(C)C>[N:11]1[CH:12]=[C:7]([C:2]([N:33]=[C:36]=[O:21])([CH3:3])[CH3:6])[CH:8]=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23708609Lithium 2-methyl-2-(5-pyrimidinyl)propionate

Product 1

HCID 543276785-(2-Isocyanatopropan-2-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of lithium 2-methyl-2-(5-pyrimidinyl)propionate (4.11 g), diphenylphosphoryl azide (13.2 g), triethylamine (4.86 g) and anhydrous tert-butyl alcohol (100 mL) was heated to reflux for 6 h, then allowed to cool and concentrated in vacuo. The residue was partitioned between chloroform (250 mL) and water (100 mL), and the chloroform was extracted, dried (MgSO4) and evaporated under reduced pressure. Chromatography on silica gel, eluting with chloroform; 5% methanol gave a partially purified sample of 2-(5-pyrimidinyl)-2-propylisocyanate as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between chloroform (250 mL) and water (100 mL)
  6. extractionthe chloroform was extracted
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. washChromatography on silica gel, eluting with chloroform

Sources & evidence

ORD record
ord-6808954e82c643a5b693cf60a6ef767f
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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