Dimethylformamide → HCID 86677965, compound

HRID 246243Notes

Reaction equation

HRID 246243 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:32]=[CH:31][C:10]2[N:11]([C:14]3[N:15]=[C:16]4[CH:22]=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:17]4=[N:18][CH:19]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1.CN([CH:36]=[O:37])C>>[Cl:6][C:7]1[CH:32]=[CH:31][C:10]2[N:11]([C:14]3[N:15]=[C:16]4[C:22]([CH:36]=[O:37])=[CH:21][N:20]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[C:17]4=[N:18][CH:19]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 71280293HCID 71280293, compound

Product 1

HCID 86677965HCID 86677965, compound

Conditions

Temperature
67.5 °C

Procedure

A solution of DMF at 5° C. was treated with phosphoryl trichloride (483 mg, 3.2 mmol) for 0.5 h. 2-(5-Chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (210 mg, 0.52 mmol) was added and the mixture was stirred at 65-70° C. for 7 h. The reaction was cooled and quenched with NaHCO3 (aq) then extracted into ethyl acetate (2×). The organics were washed with water and brine then dried (MgSO4). Purification was by flash chromatography gave 2-(5-chloro-benzoimidazol-1-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde. LCMS: (M+H)+=428.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with NaHCO3 (aq)
  3. extractionthen extracted into ethyl acetate (2×)
  4. washThe organics were washed with water and brine
  5. dry with materialthen dried (MgSO4)
  6. customPurification

Sources & evidence

ORD record
ord-9751cdb649dd4906ae82c78e5712cdaa
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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