Benzoyl chloride → HCID 21976425, compound

HRID 11755Notes

Reaction equation

HRID 11755 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[NH:8][C:7]2=[N:9][CH:10]=[CH:11][C:6]2=[C:5]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1.CCN(CC)CC.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CN(C1C=CN=CC=1)C>[C:25]([N:9]1[C:7]2[N:8]=[C:3]([N:2]([CH3:17])[CH3:1])[N:4]=[C:5]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[C:6]=2[CH:11]=[CH:10]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 178418943HCID 178418943, compound

Product 1

HCID 21976425HCID 21976425, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethyl-4-(2-furyl)-1H-pyrrolo[2,3-d]pyrimidine-2-amine (181 mg, 0.8 mmol) in THF (3 mL) was treated with Et3N, (111 μL, 0.8 mmol), benzoyl chloride (93 μL, 0.8 mmol) and a catalytic amount of DMAP, stirred at room temperature for 16 h, quenched with water, extracted with EtOAc, dried (MgSO4), concentrated in vacuo and purified by chromatography (EtOAc:Heptane, 1:9 then Heptane:DCM, 2:1) to give the title compound (76 mg) as a yellow solid.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (EtOAc

Sources & evidence

ORD record
ord-a071ae83731e44dba70337a8f6a9c26b
Source dataset
uspto-grants-2006_08
Patent number
US07098333B2

Reaction notes

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