Triethylamine → Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate

HRID 1366626Notes

Reaction equation

HRID 1366626 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.[S:40]1[CH:44]=[CH:43][C:42]([CH2:45][NH2:46])=[CH:41]1>C1COCC1.O>[CH3:4][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]([NH:46][CH2:45][C:42]2[CH:43]=[CH:44][S:40][CH:41]=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:7])([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27763813-ThiophenemethylamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86637009Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (1.413 g, 2.85 mmol) was dissolved in THF (5 mL). To this solution was added triethylamine (0.48 mL, 3.4438 mmol), followed by commercially available (3-thienylmethyl)amine (0.322 g, 2.85 mmol) which was dissolved in THF (1 mL). After stirring, 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-[(3-thienylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate as a white solid (1.6214 g, 99%). LCMS: (M+H−3Boc)+=374.1.

Workup

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

Sources & evidence

ORD record
ord-80beed6db33145ddb1d540651328e397
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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