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4-Methylpyrazole → 1-methyl-2-(1-(2-methyl-6-(4-methyl-1H-pyrazol-1-yl)pyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

HRID 2202820
Notes
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Reaction equation

HRID 2202820 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:14]1[N:19]=[C:18]([CH3:20])[N:17]=[C:16]([N:21]2[CH2:24][CH:23]([C:25]3[N:29]([CH3:30])[C:28]4[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=4[N:26]=3)[CH2:22]2)[CH:15]=1>CC(N(C)C)=O>[CH3:30][N:29]1[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[C:25]1[CH:23]1[CH2:24][N:21]([C:16]2[CH:15]=[C:14]([N:4]3[CH:3]=[C:2]([CH3:1])[CH:6]=[N:5]3)[N:19]=[C:18]([CH3:20])[N:17]=2)[CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 34064-MethylpyrazoleHCID 10796Cesium carbonateHCID 894935592-(1-(6-chloro-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

Product 1

HCID 715508051-methyl-2-(1-(2-methyl-6-(4-methyl-1H-pyrazol-1-yl)pyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Procedure

To a solution of 4-methylpyrazole (10.5 mg, 0.13 mmol) in DMA (0.65 mL) in a microwave vial was added Cs2CO3 (83 mg, 0.26 mmol) and the mixture was stirred at rt. After 15 min, Intermediate 3 (40 mg, 0.13 mmol) was added and the tube was capped, sealed, and heated at 150° C. for 3 h. The reaction was cooled to rt, filtered through a syringe filter and purified by reverse-phase preparative chromatography (5-50% acetonitrile/water+0.1% TFA) to give Example 2. 1H NMR: (500 MHz, CD3OD) δ 8.31 (m, 1H), 7.76 (m, 1H), 7.54 (m, 1H), 7.33 (m, 3H), 6.62 (s, 1H), 4.64 (m, 4H), 4.31 (m, 1H), 3.73 (s, 3H), 2.51 (s, 3H), 2.14 (s, 3H) ppm. MS: m/z=360.5 (M+H).

Workup

  1. customthe tube was capped
  2. customsealed
  3. temperatureheated at 150° C. for 3 h
  4. temperatureThe reaction was cooled to rt
  5. filtrationfiltered through a syringe
  6. filtrationfilter
  7. custompurified by reverse-phase preparative chromatography (5-50% acetonitrile/water+0.1% TFA)
  8. customto give Example 2

Sources & evidence

ORD record
ord-d6f2b1bca83d4e62b2891490c899a92c
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365562B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes