Methanol → HCID 90415997, compound

HRID 869125Notes

Reaction equation

HRID 869125 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]2[N:12]=[C:13]([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[C:14]([C:15]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[O:24][CH3:25])=[O:16])=[C:8]2[N:7]=1)C=C.CN1C(=O)CC(=O)N(C)C1=O.C(Cl)Cl.CO>C(Cl)Cl.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]2[N:12]=[C:13]([NH:26][C:27](=[O:32])[C:28]([F:30])([F:31])[F:29])[C:14]([C:15]([NH:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[O:24][CH3:25])=[O:16])=[C:8]2[N:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 69860Dimethylbarbituric acidHCID 90417420HCID 90417420, compound

Product 1

HCID 90415997HCID 90415997, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

5-(Allyloxymethyl)-N-(4-methoxy-3-pyridyl)-2-[(2,2,2-trifluoroacetyl)amino]pyrazolo[1,5-a]pyrimidine-3-carboxamide (70 mg, 0.1554 mmol), 1,3-dimethylbarbituric acid (48.53 mg, 0.3108 mmol) and Pd(PPh3)4 (17.96 mg, 0.01554 mmol) were suspended in DCM/MeOH (1.4 mL/0.35 mL) in a pressure tube. The mixture was stirred at 60° C. for ˜2.5 hrs. Further DCM (1.4 mL), MeOH (0.35 mL) and Pd(PPh3)4 (17.96 mg, 0.01554 mmol) were added and the resulting mixture was stirred at 60° C. overnight. The reaction was allowed to cool to RT, the suspended solid was collected by filtration and washed with DCM (2×1 mL) and ether (3×1 mL) to give a purple powder (53.7 mg, 84% Yield) which was used directly into next step without further purification. LC-MS (M+H)+ 411.2; 1H NMR (500 MHz, DMSO-d6) δ 11.66 (s, 1H), 10.34 (s, 1H), 9.45 (s, 1H), 9.37 (d, J=7.1 Hz, 1H), 8.29 (d, J=5.5 Hz, 1H), 7.46 (d, J=7.1 Hz, 1H), 7.23 (d, J=5.6 Hz, 1H), 5.93 (t, J=6.1 Hz, 1H), 4.81 (d, J=6.0 Hz, 2H), 4.06 (s, 3H).

Workup

  1. stirringthe resulting mixture was stirred at 60° C. overnight
  2. temperatureto cool to RT
  3. filtrationthe suspended solid was collected by filtration
  4. washwashed with DCM (2×1 mL) and ether (3×1 mL)

Sources & evidence

ORD record
ord-5127b9e6fc8b462f9a9e0a5c08fcd442
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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