Dimethylformamide → 3-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)-5-[(phenylmethyl)oxy]-pyrazolo[1,5-a]pyridine

HRID 1159945Notes

Reaction equation

CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1.[CH3:29][S:30][C:31]1[N:36]=[C:35]([C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=2)[CH:34]=[CH:33][N:32]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>O>[CH3:29][S:30][C:31]1[N:36]=[C:35]([C:37]2[C:38]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=3)=[N:14][N:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][C:20]=23)[CH:34]=[CH:33][N:32]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-amino-4-[(phenylmethyl)oxy]pyridinium 2,4,6-trimethylbenzenesulfonate (13.8 mmol; crude) and 2-(methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine (6.30 g, 9.22 mmol) in dry-DMF (70 mL) was cooled to 0° C. Aq. K2CO3 (2.75 mL, 18.4 mmol) was added. The mixture was stirred at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic phase was combined, washed with brine, and dried (MgSO4). The solvent was evaporated under reduced pressure. Chromatography on silica gel eluting with hexane/EtOAc gradient (15-50% EtOAc) gave yellow solid (460 mg).

Workup

extractionextracted with EtOAc
washwashed with brine
dry with materialdried (MgSO4)
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-64f5b57c16704a7a803a428f55c9a617
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812022B2

Reaction notes

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