Potassium Iodide → HCID 86677813, compound

HRID 1499890Notes

Reaction equation

HRID 1499890 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9](Cl)[CH3:10])=[C:4]([O:12][CH3:13])[C:3]=1[CH:14]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1.[CH3:25][C:26]1[C:34]2[C:29](=NC=N[C:33]=2[NH2:35])[NH:28][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[CH3:44][N:45](C)[CH:46]=O>C(OCC)(=O)C.O>[NH2:35][C:33]1[C:34]2[C:26]([CH3:25])=[N:27][N:28]([CH:9]([C:5]3[C:4]([O:12][CH3:13])=[C:3]([CH:14]4[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:17]4)[C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=3)[CH3:10])[C:29]=2[CH:46]=[N:45][CH:44]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 86677811HCID 86677811, compoundHCID 178434474HCID 178434474, compound

Product 1

HCID 86677813HCID 86677813, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl 3-[2,3-dichloro-5-(1-chloroethyl)-6-methoxyphenyl]azetidine-1-carboxylate (1.0 g, 2.5 mmol) and 3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.43 g, 2.9 mmol) in N,N-dimethylformamide (23 mL) was treated with cesium carbonate (1.2 g, 3.8 mmol) and potassium iodide (42 mg, 0.25 mmol) and heated at 100° C. for 10 h. The reaction mixture was diluted with ethyl acetate (75 mL) and water (75 mL). The aqueous layer was separated and reextracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, saturated sodium bicarbonate solution, and brine, dried over magnesium sulfate, filtered, and concentrated to a crude residue. The crude material was purified by flash column chromatography using methanol in dichloromethane (0%-10%) to give the desired product (0.97 g, 75%). LCMS for C23H29Cl2N6O3 (M+H)+: m/z=507.2, 509.2; Found: 507.0, 509.0.

Workup

  1. customThe aqueous layer was separated
  2. washThe combined organic layers were washed with water, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a crude residue
  6. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-69188f0aa8f24722a63c656d5983e3dc
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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