Diisopropylethylamine → HCID 86636993, compound

HRID 1366584Notes

Reaction equation

HRID 1366584 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH3:17][C:18]([O:21][C:22]([N:24]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[N:25]([C:33]1[C:38]([F:39])=[C:37](Cl)[N:36]=[C:35]([Cl:41])[N:34]=1)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH3:20][C:18]([O:21][C:22]([N:24]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[N:25]([C:33]1[C:38]([F:39])=[C:37]([NH:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:36]=[C:35]([Cl:41])[N:34]=1)[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[O:23])([CH3:17])[CH3:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 58000755Tris(1,1-dimethylethyl) 2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate

Product 1

HCID 86636993HCID 86636993, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of commercially available tetrahydro-2H-pyran-4-amine (0.122 g, 1.21 mmol) in DMF (6 mL) was cooled to 0° C. Then diisopropylethylamine (0.24 mL, 1.33 mmol) and tris(1,1-dimethylethyl)2-(2,6-dichloro-5-fluoro-4-pyrimidinyl)-1,1,2-hydrazinetricarboxylate (0.600 g, 1.21 mmol) were added. The resulting solution was left to reach room temperature and stir overnight. The mixture was extracted with ether and washed with water, and the resulting aqueous layer was extracted once with ether. The combined ether layers were dried (Na2SO4) and concentrated in vacuo. The resulting material was purified by silica gel chromatography with (5-60% ethyl acetate in hexanes, 1% triethylamine) to provide tris(1,1-dimethylethyl)2-[2-chloro-5-fluoro-6-(tetrahydro-2H-pyran-4-ylamino)-4-pyrimidinyl]-1,1,2-hydrazinetricarboxylate as a white solid (0.602 g, 89%). LCMS: (M+H−2Boc)+=362.1.

Workup

  1. waitThe resulting solution was left
  2. customto reach room temperature
  3. extractionThe mixture was extracted with ether
  4. washwashed with water
  5. extractionthe resulting aqueous layer was extracted once with ether
  6. dry with materialThe combined ether layers were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting material was purified by silica gel chromatography with (5-60% ethyl acetate in hexanes, 1% triethylamine)

Sources & evidence

ORD record
ord-b6b3bf7cb65a45978f752620d4dee181
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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