4-Methylmorpholine → HCID 67219505, compound

HRID 916773Notes

Reaction equation

HRID 916773 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[C:8](I)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.[C:24]([O:28][C:29](=[O:38])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([SH:37])[CH:32]=1)([CH3:27])([CH3:26])[CH3:25]>[Cu]I.CN(C=O)C>[C:24]([O:28][C:29](=[O:38])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([S:37][C:8]2[C:9]3[C:14]([NH2:15])=[N:13][CH:12]=[N:11][C:10]=3[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]=2)[CH:32]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 11436060(3-Mercapto-phenyl)-carbamic acid tert-butyl esterHCID 672195247-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 67219505HCID 67219505, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask with DMF (5 mL), was added 7-Cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, CuI, N-methylmorphline and (3-Mercapto-phenyl)-carbamic acid tert-butyl ester. The reaction was heated at 110° C. overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc (80 mL) and saturated sodium bicarbonate solution (60 ml). The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. Purification through flash column afforded the product as a light yellow solid (108 mg, 85%). MS: 426.1 (MH+); HPLC Rf: 6.332 min.; HPLC purity: 96%.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction mixture was extracted with EtOAc (80 mL) and saturated sodium bicarbonate solution (60 ml)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification through flash column

Sources & evidence

ORD record
ord-e2fbbe01a4f74a518d381d49c9c5b314
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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