Diisopropylethylamine → 4-(1H-Imidazol-1-yl)-2-[6-(3-methylazetidin-1-yl)pyrimidin-4-yl]-1,2-dihydro-3H-pyrazol-3-one

HRID 2039489Notes

Reaction equation

HRID 2039489 reaction equation
Cl.[CH3:2][CH:3]1[CH2:6][NH:5][CH2:4]1.Cl.Cl[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]2[C:19](=[O:20])[C:18]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[CH:17][NH:16]2)[CH:10]=1.C(N(C(C)C)C(C)C)C>O1CCCC1>[N:21]1([C:18]2[C:19](=[O:20])[N:15]([C:11]3[CH:10]=[C:9]([N:5]4[CH2:6][CH:3]([CH3:2])[CH2:4]4)[N:14]=[CH:13][N:12]=3)[NH:16][CH:17]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 251591883-Methylazetidine hydrochlorideHCID 866352552-(6-Chloropyrimidin-4-yl)-4-(1H-imidazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one hydrochloride

Product 1

HCID 444646114-(1H-Imidazol-1-yl)-2-[6-(3-methylazetidin-1-yl)pyrimidin-4-yl]-1,2-dihydro-3H-pyrazol-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43 mg (0.4 mmol) of 3-methylazetidine hydrochloride, 100 mg (0.3 mmol) of the compound from Example 13A and 174 μl (130 mg, 1.0 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine are suspended in 2 ml of tetrahydrofuran and reacted in a single mode microwave (Emrys Optimizer) at 120° C. for 4.5 h. The reaction mixture is concentrated under reduced pressure, taken up in water with addition of aqueous 1 N sodium hydroxide solution (pH=9-10) and purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). Yield: 30 mg (30% of theory)

Workup

  1. customreacted in a single mode microwave (Emrys Optimizer) at 120° C. for 4.5 h
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additiontaken up in water with addition of aqueous 1 N sodium hydroxide solution (pH=9-10)
  4. custompurified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-b8cb80d48c6a4803959f1bffac26a7ac
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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