Potassium Carbonate → HCID 178435370, compound

HRID 2053025Notes

Reaction equation

HRID 2053025 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[C:23]3[C:22]([NH2:24])=[N:21][CH:20]=[N:19][C:18]=3[NH:17][C:16]=2[CH2:25][CH3:26])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:51][O:52][C:53]([CH:55]1[CH2:58][CH:57](OS(C)(=O)=O)[CH2:56]1)=[O:54]>CN(C)C=O>[CH3:51][O:52][C:53]([C@H:55]1[CH2:58][C@H:57]([N:17]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH2:24])[C:23]=3[C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)=[C:16]2[CH2:25][CH3:26])[CH2:56]1)=[O:54]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 54092241HCID 54092241, compoundHCID 69203774HCID 69203774, compound

Product 1

HCID 178435370HCID 178435370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1.26 g (2.74 mmol) 5-(3-benzyloxy-phenyl)-6-ethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, 1.53 g (10.9 mmol) of powdered potassium carbonate and 2.92 g (10.9 mmol) 18-crown-6 ether in 12 ml dry N,N-dimethylformamide is stirred for 15 min at 80° C. 1.7 g (8.2 mmol) of 3-Methanesulfonyloxy-cyclobutanecarboxylic acid methyl ester, dissolved in 9 ml dry N,N-dimethylformamide, is added dropwise in 15 min. After stirring for 42 h at 80° C., work-up is effected by filtering the reaction mixture on hyflo and evaporating the solvent. The residue is partitioned between water and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo. The crude product is purified and separated by flash chromatography (hexane-ethyl acetate 1:2). The ratio cis to trans isomer is about 70:30 (by HPLC, Grad25).

Workup

  1. additionis added dropwise in 15 min
  2. stirringAfter stirring for 42 h at 80° C.
  3. filtrationby filtering the reaction mixture on hyflo
  4. customevaporating the solvent
  5. customThe residue is partitioned between water and ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified
  9. customseparated by flash chromatography (hexane-ethyl acetate 1:2)

Sources & evidence

ORD record
ord-8339f3eeb94a49d7b34b6eceac76b1ec
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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