Cesium carbonate → 4-(2-Cyclopropylpyrazolo[1,5-a]pyrimidin-7-ylthio)benzenamine

HRID 1951285Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.Cl[C:16]1[N:21]2[N:22]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[CH:24]=[C:20]2[N:19]=[CH:18][CH:17]=1>CN(C=O)C.CCOC(C)=O>[CH:25]1([C:23]2[CH:24]=[C:20]3[N:19]=[CH:18][CH:17]=[C:16]([S:14][C:11]4[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][CH:10]=4)[N:21]3[N:22]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of cesium carbonate (0.606 g, 1.86 mmol) and 4-aminobenzenethiol (116 mg, 0.930 mmol) in DMF (3 mL) at RT was added 7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidine (0.180 g, 0.930 mmol). The mixture was heated to 60° C. After 2 hrs the mixture was cooled to RT, diluted with EtOAc, and washed with water and brine. After drying the organic fraction with sodium sulfate, the solvent was removed in vacuo to afford 4-(2-cyclopropylpyrazolo[1,5-a]pyrimidin-7-ylthio)benzenamine, which was advanced without further purification. MS: Found M+H+=283.1.

Workup

temperatureAfter 2 hrs the mixture was cooled to RT
washwashed with water and brine
dry with materialAfter drying the organic fraction with sodium sulfate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-e443de74d4154c86a94499e9f2b0afeb
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404694B2

Reaction notes

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