5-(Piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine → 3-(1-Methyl-1H-pyrazol-4-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047115Notes

Reaction equation

HRID 2047115 reaction equation
N1CCC(C2C=C(N)N3N=CC(C4C=NC5C(C=4)=CC=CC=5)=C3N=2)CC1.C[Si](C)(C)CCOC[N:33](COCC[Si](C)(C)C)[C:34]1[N:39]2[N:40]=[CH:41][C:42]([C:43]3[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=3)=[C:38]2[N:37]=[C:36]([CH:49]2[CH2:54][CH2:53][N:52](C(OC(C)(C)C)=O)[CH2:51][CH2:50]2)[CH:35]=1.C[Si](C)(C)CCOCN(COCC[Si](C)(C)C)C1N2N=CC(C3C=NC4C(C=3)=CC=CC=4)=C2N=C(C2CCN(C(OC(C)(C)C)=O)CC2)C=1>>[CH3:48][N:46]1[CH:47]=[C:43]([C:42]2[CH:41]=[N:40][N:39]3[C:34]([NH2:33])=[CH:35][C:36]([CH:49]4[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]4)=[N:37][C:38]=23)[CH:44]=[N:45]1

Participants

4

Reactant 3

HCID 667380825-(Piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amineHCID 67494438tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylateHCID 67494469tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate

Product 1

HCID 674942323-(1-Methyl-1H-pyrazol-4-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine

Procedure

3-(1-Methyl-1H-pyrazol-4-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine was synthesized in a manner similar to the synthesis of 5-(piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine, but with tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate substituted for tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate.

Sources & evidence

ORD record
ord-261643376e834d4790ece1cbc94deac5
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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