Diisopropylethylamine → 2-(4-Oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione

HRID 2076835Notes

Reaction equation

HRID 2076835 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[CH:18][N:17]=1)=O.CCN(C(C)C)C(C)C>CN(C=O)C>[O:23]=[C:22]1[C:21]2[C:16](=[N:17][CH:18]=[N:19][CH:20]=2)[N:15]=[C:13]([CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[NH:24]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 670991574-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-pyrimidine-5-carboxylic acid amide

Product 1

HCID 1363668202-(4-Oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-pyrimidine-5-carboxylic acid amide (100 mg, 0.31 mmol) in DMF (2 mL) was treated with DIPEA (0.39 mL, 2.29 mmol) for 2 hours at 90° C. The reaction mixture was evaporated, the residue was triturated with EtOAc and filtrated to yield 2-(4-oxo-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2-ylmethyl)-isoindole-1,3-dione as a light yellow solid (73 mg, 77%). MS (m/e): 308.4 [M+H+].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was triturated with EtOAc
  3. filtrationfiltrated

Sources & evidence

ORD record
ord-fd3ff24c0568470d9a8a25ba9f0fde46
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Reaction notes

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