Ethyl Acetate → HCID 86608382, compound

HRID 882746Notes

Reaction equation

HRID 882746 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-2970e225391042e4a0a8ea079daa1d6d
Source dataset
uspto-grants-2012_08
Patent number
US08236795B2

Reaction notes

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