3-Piperidinecarboxamide → 1-(6-(2-Amino-6-methylpyrazolo[1,5-a]pyrimidin-3-yl)pyrimidin-4-yl)piperidine-3-carboxamide

HRID 490117Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([NH2:20])[C:10]=2[C:11]2[CH:16]=[C:15](S(C)=O)[N:14]=[CH:13][N:12]=2)[CH:7]=1.[NH:21]1[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22]1>CN1C(=O)CCC1>[NH2:20][C:9]1[C:10]([C:11]2[N:12]=[CH:13][N:14]=[C:15]([N:21]3[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22]3)[CH:16]=2)=[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]2[N:8]=1

Participants

Conditions

Temperature: 200 °C

Procedure

6-methyl-3-(6-(methylsulfinyl)pyrimidin-4-yl)pyrazolo[1,5-a]pyrimidin-2-amine (60 mg, 0.21 mmol) was dissolved in NMP with nipecotamide (100 mg, 0.78 mmol)and heated to 200° C. in a microwave for 20 min. The reaction mixture was purified by RP HPLC (C18, CH3CN/H2O 0.1% TFA) and the pure fractions were poured into ethyl acetate/0.5 N NaOH. The organic phase was dried over sodium sulfate and concentrated to a yellow solid which was dissolved in 1N HCl in MeOH and concentrated to the HCl salt as a yellow solid, 20 mg, 0.052 mmol, 26%. LC/MS MH+353.4

Workup

customThe reaction mixture was purified by RP HPLC (C18, CH3CN/H2O 0.1% TFA)
additionthe pure fractions were poured into ethyl acetate/0.5 N NaOH
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated to a yellow solid which
dissolutionwas dissolved in 1N HCl in MeOH
concentrationconcentrated to the HCl salt as a yellow solid, 20 mg, 0.052 mmol, 26%

Sources & evidence

ORD record: ord-1dfbe04131354aeebcbb416aa8e745be
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528138B2

Reaction notes

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