Diethyl Ether → HCID 86636984, compound

HRID 1366552Notes

Reaction equation

HRID 1366552 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[N:9]([C:17]1[C:22]([F:23])=[C:21](Cl)[N:20]=[C:19]([Cl:25])[N:18]=1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH:42]1([NH2:46])[CH2:45][CH2:44][CH2:43]1.CCOCC>CN(C=O)C>[CH3:31][C:29]([O:28][C:26]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:4])[CH3:3])=[O:7])[N:9]([C:17]1[C:22]([F:23])=[C:21]([NH:46][CH:42]2[CH2:45][CH2:44][CH2:43]2)[N:20]=[C:19]([Cl:25])[N:18]=1)[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:27])([CH3:30])[CH3:32]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86636984HCID 86636984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (0.497 g, 1.0 mmol) in DMF (5 mL) at room temperature was added diisopropylethylamine (0.19 mL, 1.10 mmol) followed immediately by commercially available cyclobutylamine (0.085 mL, 1.0 mmol). The reaction was stirred for 4 days, then ether was added, and the mixture was washed with water and the aqueous layer was back extracted. The combined organics were dried (Na2SO4), concentrated in vacuo, and azeotroped once with MeOH to provide tris(1,1-dimethylethyl)2-[2-chloro-6-(cyclobutylamino)-5-fluoro-4-pyrimidinyl]-1,1,2-hydrazinetricarboxylate as a white solid.

Workup

  1. washthe mixture was washed with water
  2. extractionthe aqueous layer was back extracted
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customazeotroped once with MeOH

Sources & evidence

ORD record
ord-103b8768fdde4b28a3da1ae52a96cb78
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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