p-Toluenesulfonic acid → HCID 58015937, compound

HRID 2189290Notes

Reaction equation

HRID 2189290 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1.CN(C=O)C.CCOC(C)=O>[C:32]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:2]3[N:3]=[CH:4][C:5]4[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=4[N:7]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)(=[O:34])[CH3:33]

Participants

7

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 73554660HCID 73554660, compound

Product 1

HCID 58015937HCID 58015937, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-chloro-7-(1-ethyl-propyl)-5,5-dimethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (20 mg, 0.075 mmol) in 1,4-dioxane (1 mL) and DMF (0.2 mL) are added 1-[4-(4-amino-phenyl)-piperazin-1-yl]-ethanone (24.5 mg, 0.11 mmol) and p-toluenesulfonic acid (17 mg, 0.089 mmol). The reaction mixture is sealed in a microwave reactor and heated at 140° C. for 30 min. The mixture is diluted with EtOAc and washed with 1N NaOH solution. The organics is dried over Na2SO4, filtered, and concentrated. The residue is purified by prep-HPLC to give 30 mg of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-5,5-dimethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one as a pale yellow solid.

Workup

  1. customThe reaction mixture is sealed in a microwave reactor
  2. washwashed with 1N NaOH solution
  3. dry with materialThe organics is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by prep-HPLC

Sources & evidence

ORD record
ord-c8db9e42e1d440769967143c8b6c0b7f
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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