Phthalic Anhydride → 2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)isoindoline-1,3-dione

HRID 1391974Notes

Reaction equation

CN(C)C(=O)C.[N:7]1[C:12]2[NH:13][CH:14]=[CH:15][C:11]=2[C:10]([NH2:16])=[N:9][CH:8]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>O>[C:17]1(=[O:22])[N:16]([C:10]2[C:11]3[CH:15]=[CH:14][NH:13][C:12]=3[N:7]=[CH:8][N:9]=2)[C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12

Participants

Conditions

Temperature: 80 °C

Procedure

To a 250 mL three-neck round bottom flask equipped with an overhead stirrer, nitrogen inlet, and thermocouple was charged 50 mL of dry N,N-dimethylacetamide followed by 5.0 g of 7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (3-1) [J. Davoll, J. Chem. Soc., 131-138 (1960)] and 11.6 g of phthalic anhydride. The resulting mixture was heated to 80° C. for 8 h and then cooled to 10° C. Water (40 mL) was added while maintaining the temperature below 15° C. The resulting slurry was aged for 4 h, then filtered, and the filter washed with 20 mL of 1:1 (v/v) dimethylacetamide/water followed by 30 mL of water. The cake was sucked dry, then washed with 50 mL of ethyl acetate. The solid was dried at 40° C. under vacuum with a nitrogen sweep to give 8.1 g of 4-phthalimido-7H-pyrrolo[2,3-d]pyrimidine (3-2); m.p. 276-277° C.

Workup

customTo a 250 mL three-neck round bottom flask equipped with an overhead stirrer, nitrogen inlet
temperaturecooled to 10° C
temperaturewhile maintaining the temperature below 15° C
filtrationfiltered
washthe filter washed with 20 mL of 1:1 (v/v) dimethylacetamide/water
customThe cake was sucked dry
washwashed with 50 mL of ethyl acetate
customThe solid was dried at 40° C. under vacuum with a nitrogen sweep

Sources & evidence

ORD record: ord-803b9b57ab9047638d0612f8abd2c06f
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07339054B2

Reaction notes

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