Dimethylformamide → HCID 68857338, compound

HRID 1783561Notes

Reaction equation

HRID 1783561 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]3[N:12]([CH:27]([CH3:29])[CH3:28])[C:13](=[O:26])[N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[C:15](=[O:16])[C:9]3=[CH:8][N:7]=2)[CH:5]=[CH:4]N=C1.[CH2:30]([N:32]([CH2:43][CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:42]=CC(N)=[CH:38][CH:37]=1)[CH3:31].C1(=O)OC(=O)CC1.CN(C)C=O>C(Cl)(Cl)Cl>[CH2:43]([N:32]([CH2:30][CH3:31])[CH2:33][CH2:34][O:35][C:36]1[CH:42]=[CH:4][C:5]([NH:1][C:6]2[N:11]=[C:10]3[N:12]([CH:27]([CH3:28])[CH3:29])[C:13](=[O:26])[N:14]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[C:15](=[O:16])[C:9]3=[CH:8][N:7]=2)=[CH:38][CH:37]=1)[CH3:44]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7922Succinic anhydrideHCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 68862069HCID 68862069, compound

Product 1

HCID 68857338HCID 68857338, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
180 °C

Procedure

A mixture of 700 mg (1.78 mmol) of 7-(imidazol-1-yl)-1-isopropyl-3-(4-methoxybenzyl)-1H-pyrimido[4,5-d]pyrimidine-2,4-dione and 1.1 g (5.35 mmol) of 4-(2-diethylaminoethoxy)aniline is heated at 180° C. for 4 hours, then cooled. To the reaction mixture is added 357 mg (3.6 mmol) of succinic anhydride, 1 mL of chloroform, and 3 mL of dimethylformamide. The reaction mixture is heated at 50° C. for 2 hours, cooled, and diluted with chloroform. The mixture is washed with a saturated solution of sodium bicarbonate and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated. The residue is chromatographed on silica eluting with 5:95 methanol/chloroform to give a yellow solid which is crystallized from methanol/water to give 590 mg (61%) of the title compound: mp 139-141° C.

Workup

  1. temperaturecooled
  2. temperatureThe reaction mixture is heated at 50° C. for 2 hours
  3. temperaturecooled
  4. washThe mixture is washed with a saturated solution of sodium bicarbonate and brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica eluting with 5:95 methanol/chloroform
  9. customto give a yellow solid which
  10. customis crystallized from methanol/water

Sources & evidence

ORD record
ord-4d1bd65c1cad471aaf49b4c5d19295ec
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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