Sodium Carbonate → 6-chloro-3-methoxy-4-(2-methylpyrimidin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 588160Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8](=O)[C:9]#[CH:10])[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.Cl.[C:37]([NH2:40])(=[NH:39])[CH3:38].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][N:40]=[C:37]([CH3:38])[N:39]=2)[C:5]2[C:12]([O:34][CH3:35])=[N:13][N:14]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)prop-2-yn-1-one (60B, 63 mg, 0.132 mmol) was dissolved in acetonitrile (3 ml), charged with acetamidine hydrochloride (14.95 mg, 0.158 mmol) and sodium carbonate (34.9 mg, 0.330 mmol) and allowed to stir at 70° C. for 2 h. The solution was filtered through a syringe filter and the solvents were removed in vacuo. The residue was purified on silica gel 2-25% EtOAc/DCM to afford 6-chloro-3-methoxy-4-(2-methylpyrimidin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (63B, 58 mg, 0.112 mmol, 85% yield). MS: [M+H]+ m/z 518.

Workup

filtrationThe solution was filtered through a syringe
filtrationfilter
customthe solvents were removed in vacuo
customThe residue was purified on silica gel 2-25% EtOAc/DCM

Sources & evidence

ORD record: ord-9a4d090bd7f84d2496364d1993303bb5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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