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Sodium hydride → 2,4-dichloro-3-({5-cyclopropyl-3-[5-methoxy-4-(pyridin-4-ylamino) pyrimidin-2-yl]-4-methyl-1H-pyrazol-1-yl}methyl)benzoic acid

HRID 1774541
Notes
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Reaction equation

HRID 1774541 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:9]3[N:14]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[C:12]([O:22][CH3:23])=[CH:11][N:10]=3)[C:5]=2[CH3:24])[CH2:3][CH2:2]1.Br[CH2:26][C:27]1[C:28]([Cl:38])=[C:29]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:30]([O:32]C)=[O:31].[H-].[Na+]>C1COCC1>[Cl:38][C:28]1[C:27]([CH2:26][N:8]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[C:5]([CH3:24])[C:6]([C:9]3[N:14]=[C:13]([NH:15][C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[C:12]([O:22][CH3:23])=[CH:11][N:10]=3)=[N:7]2)=[C:36]([Cl:37])[CH:35]=[CH:34][C:29]=1[C:30]([OH:32])=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15477480Methyl 3-(bromomethyl)-2,4-dichlorobenzoateHCID 896490232-(5-cyclopropyl-4-methyl-1H-pyrazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine

Product 1

HCID 716115972,4-dichloro-3-({5-cyclopropyl-3-[5-methoxy-4-(pyridin-4-ylamino) pyrimidin-2-yl]-4-methyl-1H-pyrazol-1-yl}methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

200 mg of 2-(5-cyclopropyl-4-methyl-1H-pyrazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine 1-16-1 (0.62 mmol, 1.0 eq.), 184.86 mg of methyl 3-(bromomethyl)-2,4-dichlorobenzoate (0.62 mmol, 1.0 eq.) and 31.0 mg of 60% sodium hydride in paraffin oil were suspended in 6.3 mL of dry THF and stirred for 20 hours at rt. The reaction mixture was partitioned between water and DCM/propan-2-ol 4:1. The separated aqueous layer was extracted three times with DCM/propan-2-ol 4:1. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The purification by flash chromatography and preparative HPLC of the residue provided 37.5 mg (0.07 mmol, 11%) of analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between water and DCM/propan-2-ol 4:1
  2. extractionThe separated aqueous layer was extracted three times with DCM/propan-2-ol 4:1
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe purification by flash chromatography and preparative HPLC of the residue
  6. customprovided 37.5 mg (0.07 mmol, 11%) of analytically pure target compound

Sources & evidence

ORD record
ord-8f394887b2f04563946bf139ce51e042
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260412B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes