3,3-Difluoropyrrolidine hydrochloride → 5-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(4-methoxy-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 400851Notes

Reaction equation

HRID 400851 reaction equation
C(C1N=C(N2CCOCC2)C2N=NN(CC3C=CC(OC)=CC=3)C=2N=1)(C)(C)C.[C:29]([C:33]1[N:34]=[C:35](Cl)[C:36]2[N:41]=[N:40][N:39]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[C:37]=2[N:38]=1)([CH3:32])([CH3:31])[CH3:30].Cl.[F:53][C:54]1([F:59])[CH2:58][CH2:57][NH:56][CH2:55]1>>[C:29]([C:33]1[N:34]=[C:35]([N:56]2[CH2:57][CH2:58][C:54]([F:59])([F:53])[CH2:55]2)[C:36]2[N:41]=[N:40][N:39]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[C:37]=2[N:38]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 3

HCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 715580514-(5-tert-butyl-3-(4-methoxy benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)morpholineHCID 866832995-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 715580535-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-(4-methoxy-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

In analogy to the procedure described for the synthesis of 4-(5-tert-butyl-3-(4-methoxy benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)morpholine (example 58, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo [4,5-d]pyrimidine and 3,3-difluoropyrrolidine hydrochloride and isolated as white solid (271 mg, 83%). MS (m/e): 403.4 (MH+).

Sources & evidence

ORD record
ord-2310ca8e6fc84b2594bb478b4bd39698
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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