Phthalimide → HCID 178508598, compound

HRID 2052988Notes

Reaction equation

HRID 2052988 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:28][C@H:27]([CH2:29]O)[CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1(=[O:60])[NH:54][C:53](=[O:55])[C:52]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:51]12.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)=[CH:9][N:8]([C@H:25]3[CH2:26][C@H:27]([CH2:29][N:54]4[C:50](=[O:60])[C:51]5[C:52](=[CH:56][CH:57]=[CH:58][CH:59]=5)[C:53]4=[O:55])[CH2:28]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178508604HCID 178508604, compound

Product 1

HCID 178508598HCID 178508598, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 g (12.48 mmol) of trans-{3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutyl}-methanol, which is prepared as described in Example 47(b) of WO 97/28161, in 100 ml of dry THF are added under argon 4.91 g (18.72 mmol) of triphenylphosphine and 2.75 g (18.7 mmol) of phthalimide; 3.36 g (3.02 ml; 18.7 mmol) of diethyl azodicarboxylate (96%) are added dropwise thereto. The reaction mixture is stirred at RT for 27 h. The reaction mixture is concentrated to dryness and the crude compound is purified by flash-chromatography (ethylacetate) to obtain trans-2-{3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutylmethyl}-isoindole-1,3-dione. Analytical HPLC: tR=12.12 min (Grad 1); ES-MS: m/eo=529.9.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. customthe crude compound is purified by flash-chromatography (ethylacetate)

Sources & evidence

ORD record
ord-82702000842d4d3ab599212f3757cba4
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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