Sodium hydride → HCID 123379255, compound

HRID 2174188Notes

Reaction equation

HRID 2174188 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[S:7][C:8]=1[C:9](=[N:11][OH:12])[CH3:10].[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23](S(C)(=O)=O)[N:22]=1>CN(C=O)C>[Cl:3][C:4]1[N:5]=[C:6]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[S:7][C:8]=1[C:9](=[N:11][O:12][C:23]1[N:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]([O:20][CH3:19])[N:22]=1)[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 131732978HCID 131732978, compound

Product 1

HCID 123379255HCID 123379255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (NaH, 60% dispersion in mineral oil: 48 mg, 1.2 mmol) in DMF (2 ml) was added a solution of 1-[4-chloro-2-(3-pyridyl)thiazol-5-yl]ethanone oxime (253.7 mg, 1 mmol) in DMF (3 ml), and the resulting frothy mixture was stirred for 1 hour. After that, 4,6-dimethoxy-2-methylsulfonyl-pyrimidine (218 mg, 1 mmol) was added into the above solution. The homogeneous, dark-red solution was stirred at ambient temperature for 18 hours. The precipitated brown solid was filtered and washed with water and dried under vacuum to afford the brown solid of 1-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-(4,6-dimethoxypyrimidin-2-yl)oxy-ethanimine in a mixture of Z and E-isomers. 1H NMR (300 Mz, CDCl3): δ: 9.16 (s, 1H), 8.70 (d, 1H, J=4.8 Hz), 8.24 (m, 1H), 7.41 (m, 1H), 5.84 (m, 1H), 3.97 (m, 6H), 2.79 (m, 2H). MS (ESI): 392 (M+1), 414 (M+Na).

Workup

  1. stirringThe homogeneous, dark-red solution was stirred at ambient temperature for 18 hours
  2. filtrationThe precipitated brown solid was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4dbf5e04a47e46b2919ca9303cee5346
Source dataset
uspto-grants-2015_06
Patent number
US09060519B2

Reaction notes

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