Trifluoroacetic acid → HCID 9821181, compound

HRID 1783528Notes

Reaction equation

HRID 1783528 reaction equation
[CH3:1][N:2]([CH3:28])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]4[N:22]([CH3:27])[C:23](=[O:26])[NH:24][CH2:25][C:19]4=[CH:18][N:17]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.FC(F)(F)C(O)=O.CC(C)([O-])C.[K+]>O1CCCC1>[CH3:1][N:2]([CH3:28])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:21]=[C:20]4[N:22]([CH3:27])[C:23](=[O:26])[N:24]=[CH:25][C:19]4=[CH:18][N:17]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 23665647Potassium tert-butoxideHCID 54229398HCID 54229398, compound

Product 1

HCID 9821181HCID 9821181, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared from 170 mg (0.26 mmol) of 7-{4-[4-(dimethylamino)piperidin-1-yl]phenylamino}-1-methyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 233 mg (2.07 mmol) of potassium tert-butoxide in 20 mL of tetrahydrofuran. The reaction mixture is stirred for 6 days, and the workup is done as described in the general procedure, including a back-extraction of the combined aqueous phase with chloroform. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated. The semi-solid is triturated in diethyl ether/hexane, and the powder is collected and dried to give 64 mg (60%) of the title compound: mp 198-202° C. (dec).

Workup

  1. extractiona back-extraction of the combined aqueous phase with chloroform
  2. dry with materialThe combined organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe semi-solid is triturated in diethyl ether/hexane
  6. customthe powder is collected
  7. customdried

Sources & evidence

ORD record
ord-3aa7af4bf0824f759dd2992775b1e50f
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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