Ethyl Acetate → HCID 86608383, compound

HRID 882750Notes

Reaction equation

HRID 882750 reaction equation
[NH:1]([C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:6]=[C:5]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH:4]=1)[NH2:2].[N:21]([O-])=O.[Na+].C(OCC)(=O)C>C(O)(=O)C.O>[N:1]([C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:6]=[C:5]([O:15][CH2:16][C:17]([CH3:20])([OH:19])[CH3:18])[CH:4]=1)=[N+:2]=[N-:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 68514795HCID 68514795, compound

Product 1

HCID 86608383HCID 86608383, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-(6-hydrazino-2-morpholin-4-yl-pyrimidin-4-yloxy)-2-methyl-propan-2-ol was dissolved in glacial acetic acid (30 mL). To this solution was added a solution of sodium nitrite (700 mg) in water (4 mL). The reaction was stirred for ten minutes, and poured into ethyl acetate (100 mL). The organic layer was then washed with water (100 mL) and 10% sodium carbonate (2×100 mL). The organic layer was dried over magnesium sulfate and evaporated to give 1-(6-Azido-2-morpholin-4-yl-pyrimidin-4-yloxy)-2-methyl-propan-2-ol, which was used without purification in the next reaction.

Workup

  1. washThe organic layer was then washed with water (100 mL) and 10% sodium carbonate (2×100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-94c5e64fbf0e4a82ac3d783ff8f5e7dd
Source dataset
uspto-grants-2012_08
Patent number
US08236795B2

Reaction notes

Loading…