Dichloromethane → HCID 44197664, compound

HRID 1970944Notes

Reaction equation

HRID 1970944 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22](B4OC(C)(C)C(C)(C)O4)[CH:23]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:33][C:34]1[CH:39]=[C:38](Cl)[N:37]=[C:36]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[N:35]=1.C(Cl)Cl>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:33][C:34]1[N:35]=[C:36]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[N:37]=[C:38]([C:22]2[CH:23]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:10]([N:7]4[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]4)=[O:11])=[CH:13][CH:14]=3)[CH:19]=[N:20][CH:21]=2)[CH:39]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 120574654,6-dichloro-2-(2-pyridinyl)pyrimidineHCID 68754506HCID 68754506, compound

Product 1

HCID 44197664HCID 44197664, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of (4-Isopropylpiperazin-1-yl)(4-(5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)pyridin-3-yl)-phenyl)-methanone (Int. I) (1.5 eq, 402 mg) in DME (1 ml) and 2M sodium carbonate (0.62 ml) is treated with 4,6-dichloro-2-pyridin-2-yl-pyrimidine (Int. C) (1 eq, 139 mg) and placed under an atmosphere of argon. PdCl2(dppf).DCM (0.1 eq. 45 mg) is added and the reaction mixture is heated using microwave radiation at 90° C. for 90 minutes. After cooling to room temperature, the mixture is partitioned between DCM/water and the organic portion is separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue is purified by chromatography on silica eluting with 0-10% MeOH in DCM to afford the title compound [M+H]+=499/501 as a solid.

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 90° C.
  3. customfor 90 minutes
  4. customthe mixture is partitioned between DCM/water
  5. customthe organic portion is separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue is purified by chromatography on silica eluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-7d860ff69b4042a9bfc18037fbcac467
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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