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Diisopropylethylamine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[(R)-1-(3-methyl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-3-yl]-amine

HRID 451424
Notes
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Reaction equation

HRID 451424 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11]C2)[S:6][N:5]=1.[CH2:16]([C:23]1[CH:28]=[C:27]([CH3:29])[N:26]=[C:25](Cl)[N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.O>[CH2:16]([C:23]1[CH:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH:15][C@@H:12]2[CH2:13][CH2:14][N:9]([C:7]3[S:6][N:5]=[C:4]([CH3:3])[N:8]=3)[CH2:11]2)[N:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 673442811-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-amine dihydrochlorideHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 67344305(4-Benzyl-6-methyl-pyrimidin-2-yl)-[(R)-1-(3-methyl-[1,2,4]thiadiazol-5-yl)-pyrrolidin-3-yl]-amine

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(3-methyl-[1,2,4]thiadiazol-5-yl)-piperidin-4-ylamine dihydrochloride (54.2 mg, 0.2 mmol), 4-benzyl-2-chloro-6-methyl-pyrimidine (48.1 mg, 0.22 mmol)) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in dioxane (0.6 mL) was heated at 200° C. in a microwave oven for 1 hour. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc as eluent. The title compound was obtained as a yellow viscous oil (22 mg, 29%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel with EtOAc as eluent

Sources & evidence

ORD record
ord-03bba97873c043a796770718b50c609a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486967B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes