(S)-(+)-2-(Methoxymethyl)pyrrolidine → 5-tert-Butyl-3-(2-chloro-benzyl)-7-((S)-2-methoxymethyl-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 400836Notes

Reaction equation

HRID 400836 reaction equation
C(C1N=[C:7]([N:22]2C[CH2:26][O:25][CH2:24][CH2:23]2)[C:8]2N=NN(CC3C=CC=CC=3Cl)[C:9]=2N=1)(C)(C)C.[C:28]([C:32]1[N:33]=[C:34](Cl)[C:35]2[N:40]=[N:39][N:38]([CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[Cl:48])[C:36]=2[N:37]=1)([CH3:31])([CH3:30])[CH3:29].COC[C@@H]1CCCN1>>[C:28]([C:32]1[N:33]=[C:34]([N:22]2[CH2:7][CH2:8][CH2:9][C@H:23]2[CH2:24][O:25][CH3:26])[C:35]2[N:40]=[N:39][N:38]([CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[Cl:48])[C:36]=2[N:37]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 3

HCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 14339535-tert-Butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 866832845-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 715580495-tert-Butyl-3-(2-chloro-benzyl)-7-((S)-2-methoxymethyl-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-3-(2-chloro-benzyl)-7-morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 1, step c), the title compound was prepared from 5-tert-butyl-7-chloro-3-(2-chlorobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (S)-2-(methoxymethyl)pyrrolidine and isolated as light-yellow gum (12.0 mg, 61%). MS (m/e): 415.4 (MH+).

Sources & evidence

ORD record
ord-9c8a87b3d4cf4cb0805e6d3a09b259fe
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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