Ethyl Acetate → HCID 86608382, compound

HRID 641173Notes

Reaction equation

HRID 641173 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([NH:18][NH2:19])[N:15]=[C:14]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:13]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[N:27]([O-])=O.[Na+].C(OCC)(=O)C>C(O)(=O)C.O>[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N:18]=[N+:19]=[N-:27])[N:15]=[C:14]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:13]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 68518548HCID 68518548, compound

Product 1

HCID 86608382HCID 86608382, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

[2-(6-hydrazino-2-morpholin-4-yl-pyrimidin-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester was dissolved in glacial acetic acid (30 mL). To this solution was added a solution of sodium nitrite (1.3 g) 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 [2-(6-azido-2-morpholin-4-yl-pyrimidin-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester, 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-2a14b0fea93842a9ba04ba920cddaf6b
Source dataset
uspto-grants-2010_04
Patent number
US07696202B2

Reaction notes

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