Trifluoroacetic acid → 1-Cyclopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1783513Notes

Reaction equation

HRID 1783513 reaction equation
[CH:1]1([N:6]2[C:11]3=[N:12][C:13](S(C)=O)=[N:14][CH:15]=[C:10]3[CH2:9][NH:8][C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([N:27]5[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]5)=[CH:25][CH:26]=4)=[N:14][CH:15]=[C:10]3[CH2:9][NH:8][C:7]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 688593421-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 571665711-Cyclopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-oneYield 80%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2.0 g (7.1 mmol) of 1-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 2.7 g (14.3 mmol) of 1-(4-aminophenyl)-4-methylpiperazine in 32 mL of acetonitrile is added 2.75 mL (35.7 mmol) of trifluoroacetic acid. The mixture is heated at 85° C. overnight. The cooled reaction mixture is diluted with ethyl acetate and washed two times with saturated aqueous sodium bicarbonate solution and once with brine. The combined aqueous phase is back extracted with dichloromethane. The combined organic phase is dried over magnesium sulfate and concentrated. The dark solid residue is stirred for 2 hours in 30 mL of 1:1 dichloromethane/ethyl acetate, filtered, washed with ethyl acetate, and dried to give 2.3 g (80%) of the title compound: mp 236-239° C. (dec).

Workup

  1. customThe cooled reaction mixture
  2. washwashed two times with saturated aqueous sodium bicarbonate solution
  3. extractionThe combined aqueous phase is back extracted with dichloromethane
  4. dry with materialThe combined organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. filtrationfiltered
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-fe860b43c69544fc840aaf097b623f83
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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