Water → (E)-methyl 2-[2-(6-azidopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

HRID 1836104Notes

Reaction equation

HRID 1836104 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[N:11]=[CH:10][N:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[C:19](=[CH:24]\[O:25][CH3:26])/[C:20]([O:22][CH3:23])=[O:21])[CH:7]=1.O>CN(C=O)C>[N:1]([C:6]1[N:11]=[CH:10][N:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[C:19](=[CH:24]\[O:25][CH3:26])/[C:20]([O:22][CH3:23])=[O:21])[CH:7]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 86592259(E)-methyl 2-[2-(6-azidopyrimidin-4-yloxy)phenyl]-3-methoxypropenoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (0.25 g) was added to a solution of (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.0 g) in DMF (30 ml). The reaction mixture was stirred for 2 hours at room temperature, then for 6 hours at 50° C. After cooling, the reaction mixture was poured into water and extracted with ether (3×100 ml). The combined extracts were washed with brine, dried and concentrated to give (E)-methyl 2-[2-(6-azidopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (1.02 g, 99%) as an oil; 1H NHR: δ 3.51 (3H, s), 3.65 (3H, s), 6.12 (1H, s), 7.0-7.35 (4H, m), 7.37 (1H, s), mass 8.47 (1H, s) ppm; IR maxima (film): 2135, 1711, 1635 cm−1.

Workup

  1. waitfor 6 hours at 50° C
  2. temperatureAfter cooling
  3. extractionextracted with ether (3×100 ml)
  4. washThe combined extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b4ca12c4e7a41e88350c48c1ac5becb
Source dataset
uspto-grants-2004_08
Patent number
US06777412B2

Reaction notes

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