Potassium cyanate → HCID 178514100, compound

HRID 2053003Notes

Reaction equation

HRID 2053003 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:16])[C:10]=3[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8]2)[CH2:4]1.[O-:31][C:32]#[N:33].[K+]>CO>[NH2:16][C:15]1[C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)=[CH:8][N:7]([C@H:5]3[CH2:4][C@H:3]([CH2:2][NH:1][C:32]([NH2:33])=[O:31])[CH2:6]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 178511295HCID 178511295, compound

Product 1

HCID 178514100HCID 178514100, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg (0.125 mmol) of trans-7-(3-aminomethyl-cyclobutyl)-5-(3-benzyloxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine in 5 ml of methanol is added 45 mg (0.561 mmol) of potassium cyanate (Aldrich, Buchs, Switzerland). The mixture is refluxed for one week. After concentration to dryness, the residue is purified by flash-chromatography (dichloromethane:methanol=9:1) to provide trans-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-urea. Analytical HPLC: tR=6.43 min (Grad 2); ES-MS: m/eo=443.0.

Workup

  1. temperatureThe mixture is refluxed for one week
  2. concentrationAfter concentration to dryness
  3. customthe residue is purified by flash-chromatography (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-9dc53ff0611345e7ac07ba6c6393574d
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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