Triethylamine → Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(2-furanylmethyl)(methyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

HRID 1366636Notes

Reaction equation

HRID 1366636 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(CC)CC)C.[O:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[CH2:45][NH:46][CH3:47]>C1COCC1.O>[CH3:31][C:29]([O:28][C:26]([N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:1])[CH3:3])=[O:7])[N:9]([C:17]1[C:22]([F:23])=[C:21]([N:46]([CH2:45][C:41]2[O:40][CH:44]=[CH:43][CH:42]=2)[CH3:47])[N:20]=[C:19]([Cl:25])[N:18]=1)[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:27])([CH3:32])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 78492N-MethylfurfurylamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86637016Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(2-furanylmethyl)(methyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylateYield 101.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (6.22 g, 12.54 mmol) was dissolved in THF (15 mL). To this solution was added triethylamine (2.1 mL, 15.0667 mmol), followed by commercially available (2-furanylmethyl)methylamine (1.394 g, 12.32 mmol) which was dissolved in THF (3 mL). The reaction was left to stir overnight. Then the reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate. The organics were dried (Na2SO4) and concentrated to produce tris(1,1-dimethylethyl)2-{2-chloro-5-fluoro-6-[(2-furanylmethyl)(methyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate as a beige solid (7.1439 g). LCMS: (M+H)+=572.3.

Workup

  1. waitThe reaction was left
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7969839eace948bbb277ccc33fd1e68c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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