Trifluoroacetic acid → 2-[2-(2-Amino-3-phenyl-propylamino)-1-methyl-6-oxo-4-pyridin-4-yl-1,6-dihydro-pyrimidin-5-yl]-isoindole-1,3-dione

HRID 1826528Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:26])[N:4]([CH3:25])[C:5]([NH:14][CH2:15][CH:16]([NH2:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.[C:27]1(=O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[O:28]1.C(O)(C(F)(F)F)=O>CN(C=O)C.C(Cl)Cl>[NH2:24][CH:16]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:15][NH:14][C:5]1[N:4]([CH3:25])[C:3](=[O:26])[C:2]([N:1]2[C:27](=[O:28])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]2=[O:36])=[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-amino-2-(2-amino-3-phenyl-propylamino)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (100 mg, 0.22 mmol), and isobenzofuran-1,3-dione (50 mg, 0.33 mmol) in DMF (0.5 mL) was heated under microwave irradiation (150° C.) for 10 min. The cooled mixture was diluted with CH2Cl2 (2 mL) followed by the addition of TFA (1 nL). After being stirred at room temperature for 6 h, the mixture was concentrated, partitioned between NaHCO3 (aq) and CH2Cl2. The organic residue was purified on silica (1–10% MeOH in CH2Cl2) to afford the desired product as a light yellow solid. M+1 481.

Workup

concentrationthe mixture was concentrated
custompartitioned between NaHCO3 (aq) and CH2Cl2
customThe organic residue was purified on silica (1–10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-c3d7c8e3aa394a2fa0a8de7b500b5c51
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049318B2

Reaction notes

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