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

HRID 1366605Notes

Reaction equation

HRID 1366605 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.[CH3:40][NH:41][CH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1>C1COCC1.O>[CH3:4][C:2]([O:5][C:6]([N:8]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[N:9]([C:17]1[C:22]([F:23])=[C:21]([N:41]([CH3:40])[CH2:42][C:43]2[S:44][CH:45]=[CH:46][N:47]=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])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18939834Methyl((1,3-thiazol-2-yl)methyl)amineHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86637002Tris(1,1-dimethylethyl) 2-{2-chloro-5-fluoro-6-[methyl(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylateYield 109.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (1.16 g, 2.339 mmol) was dissolved in THF (5 mL). To this solution was added triethylamine (0.39 mL, 2.8 mmol), followed by N-methyl-1-(1,3-thiazol-2-yl)methanamine (0.30 g, 2.3437 mmol) in THF (2 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-[methyl(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}-1,1,2-hydrazinetricarboxylate as a white solid (1.51 g). LCMS: (M+H−Boc)+=489.1.

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-e91f002ecc694cd6b68b146b7055d1ba
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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