Dimethylformamide → HCID 69307829, compound

HRID 2375273Notes

Reaction equation

HRID 2375273 reaction equation
Br[C:2]1[C:3]([C:23]2[N:27]([CH2:28][CH3:29])[C:26]([CH3:30])=[N:25][CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:22])(=[O:21])[NH:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:31][N:32](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:31]([C:2]1[C:3]([C:23]2[N:27]([CH2:28][CH3:29])[C:26]([CH3:30])=[N:25][CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([S:15](=[O:22])(=[O:21])[NH:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:13][CH:14]=2)=[N:6][CH:7]=1)#[N:32]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 17933126HCID 17933126, compound

Product 1

HCID 69307829HCID 69307829, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

A suspension of 5-bromo-4-(1-ethyl-2-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Method 80; 0.35 g, 0.70 mmol), zinc cyanide (0.05 g, 0.42 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.02 g, 0.02 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.03 g, 0.05 mmol) in DMF (7 ml, 0.1M) was degassed (N2 purge), then heated at 120° C. for 48 h. The mixture was cooled and filtered through diatomaceous earth, then concentrated in vacuo and the residue was purified by flash silica chromatography DCM:MeOH (97:3) to give the title compound as a yellow oil (80 mg, 26%). NMR 1.22 (t, 3H), 2.52 (s, 3H), 3.15 (q, 2H), 3.27 (s, 3H), 3.42 (t, 2H), 4.41 (q, 2H), 5.08 (t, 1H), 7.75 (d, 1H), 7.83 (d, 1H), 7.90 (s, 1H), 8.18 (s, 1H), 8.68 (s, 1H); m/z 442.

Workup

  1. customwas degassed
  2. custom(N2 purge)
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through diatomaceous earth
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash silica chromatography DCM:MeOH (97:3)

Sources & evidence

ORD record
ord-440a16301e2248e4b670c76e5f34d72d
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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