Water → 5-Phenyl-3-pyridin-2-yl-6,7-dihydro-pyrazolo[1,5-a]pyrimidin-2-ylamine

HRID 490113Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([NH2:17])[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=1.Cl.CN(C)CCC([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O.O>CN(C=O)C>[C:25]1([C:3]2[CH2:2][CH2:7][N:6]3[N:8]=[C:9]([NH2:17])[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[C:5]3[N:4]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 160 °C

Procedure

6-Bromo-3-pyridin-2-yl-pyrazolo[1,5-a]pyrimidin-2-ylamine (0.52 g, 3.01 mmol) and 3-dimethylamino-1-phenyl-propan-1-one hydrochloride (0.64 g, 3.01 mmol) were suspended in dry DMF (10 mL). The mixture was heated at 160° C. for 3 hours with stirring. After allowing the reaction to cool down to room temperature, the mixture was poured into cold water. The resulting precipitate was filtered and dried to afford the title compound as a yellow solid (0.79 g, 93% yield). MS (ES+) 290. δH (DMSO-d6) 3.3 (2H, m), 4.1 (2H, m), 6.1 (2H, s), 7.2 (1H, m), 7.7 (4H, m), 7.9 (1H, t), 8.2 (1H, m), 8.4 (1H, d), 8.6 (1H, d).

Workup

customthe reaction
temperatureto cool down to room temperature
filtrationThe resulting precipitate was filtered
customdried

Sources & evidence

ORD record: ord-0bb7374907bc47e0a5ad29a4b06768c1
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528138B2

Reaction notes

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