Triethylamine → HCID 86637019, compound

HRID 1366652Notes

Reaction equation

HRID 1366652 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][CH2:46][NH2:47])=[CH:41]1>C1COCC1.O.[Na+].[Cl-]>[CH3:3][C:2]([O:5][C:6]([N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[N:9]([C:17]1[C:22]([F:23])=[C:21]([NH:47][CH2:46][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])([CH3:16])[CH3:15])=[O:11])=[O:7])([CH3:1])[CH3:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 122587372-(3-Thienyl)ethanamineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86637019HCID 86637019, compoundYield 109.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (1.84 g, 3.71 mmol) was dissolved in THF (5 mL). To this solution was added triethylamine (0.62 mL, 4.4482 mmol), followed by [2-(3-thienyl)ethyl]amine (0.470 g, 3.70 mmol) which was semi-suspended in THF (15 mL). The reaction was left to stir overnight, then diluted with water and saturated NaCl. The aqueous layer was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated to produce tris(1,1-dimethylethyl)2-(2-chloro-5-fluoro-6-{[2-(3-thienyl)ethyl]amino}-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate as an orange oil (2.389 g). LCMS: (M+H)+=588.3.

Workup

  1. waitThe reaction was left
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6582bcd48964382b0bed379ade52fc5
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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