Dimethylformamide → HCID 86667368, compound

HRID 334150Notes

Reaction equation

HRID 334150 reaction equation
CNC([C:5]1[NH:6][C:7]2[C:12]([N:13]=1)=[C:11]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[N:10]=[C:9]([Cl:20])[N:8]=2)=O.[C:21](=O)([O-])[O-].[Cs+].[Cs+].[CH3:27][N:28]([CH:30]=[O:31])[CH3:29]>O>[Cl:20][C:9]1[N:10]=[C:11]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:12]2[N:13]=[C:5]3[N:6]([C:7]=2[N:8]=1)[CH2:21][CH2:27][N:28]([CH3:29])[C:30]3=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 178485563HCID 178485563, compound

Product 1

HCID 86667368HCID 86667368, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-6-morpholin-4-yl-9H-purine-8-carboxylic acid methylamide (56 mg, 0.19 mmol) 1,2-dibromoethane (0.058 mL, 0.68 mmol) and cesium carbonate (0.25 g, 0.76 mmol) in DMF (2 mL) was heated at 100° C. for 2 h, then cooled, diluted with water and extracted five times with ethyl acetate. The combined extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated twice with diethyl ether and the solid was dried under vacuum to give 3-Chloro-7-methyl-1-morpholin-4-yl-6,7-dihydro-5H-2,4,4b,7,9-pentaaza-fluoren-8-one (47 mg, 77%). LCMS RT=2.36, [M+H]+=323/32

Workup

  1. temperaturecooled
  2. extractionextracted five times with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was triturated twice with diethyl ether
  6. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-8f559a29159f4a94bfa4beccf6228985
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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