Cesium carbonate → HCID 67974518, compound

HRID 2046199Notes

Reaction equation

[O:1]([CH2:8][C:9]1[CH:18]=[C:12]2[C:13](=[O:17])[NH:14][CH2:15][CH2:16][N:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:60]1[N:65]=[C:64]([O:66][CH3:67])[C:63]([F:68])=[CH:62][N:61]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:68][C:63]1[C:64]([O:66][CH3:67])=[N:65][C:60]([N:14]2[CH2:15][CH2:16][N:11]3[N:10]=[C:9]([CH2:8][O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:18]=[C:12]3[C:13]2=[O:17])=[N:61][CH:62]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Palladium (II) acetate (2.79 mg, 0.012 mmol) was added to a stirred suspension of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (100 mg, 0.41 mmol), cesium carbonate (0.18 g, 0.57 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (17 mg, 0.037 mmol) and 2-chloro-5-fluoro-4-methoxypyrimidine (0.2 g, 1.23 mmol) in a sealed tube and under nitrogen. The reaction mixture was stirred at 120° C. for 16 hours. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(5-fluoro-4-methoxy-pyrimidin-2-yl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (50 mg, 33% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 4.10 (s, 3H), 4.41-4.57 (m, 4H), 5.12 (s, 2H), 6.93-7.04 (m, 3H), 7.09 (s, 1H), 7.27-7.34 (m, 2H), 8.28 (d, J=2.3 Hz, 1H).

Workup

customThe solvent was evaporated in vacuo
customthe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
customThe desired fractions were collected
customthe solvents evaporated in vacuo

Sources & evidence

ORD record: ord-9d689a46633244cb859a61afb2ce46a2
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592422B2

Reaction notes

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