5-Chloro-2-(pyrrolidin-3-YL)pyrimidine → 1-Hydroxy-4-adamantyl 3-(5-chloropyrimidin-2-yl)pyrrolidine-1-carboxylate

HRID 1752322Notes

Reaction equation

HRID 1752322 reaction equation
Cl[C:2]([O:4][CH:5]1[CH:12]2[CH2:13][C:8]3([OH:15])[CH2:9][CH:10]([CH2:14][CH:6]1[CH2:7]3)[CH2:11]2)=[O:3].[Cl:16][C:17]1[CH:18]=[N:19][C:20]([CH:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)=[N:21][CH:22]=1>>[Cl:16][C:17]1[CH:18]=[N:19][C:20]([CH:23]2[CH2:27][CH2:26][N:25]([C:2]([O:4][CH:5]3[CH:12]4[CH2:13][C:8]5([OH:15])[CH2:9][CH:10]([CH2:14][CH:6]3[CH2:7]5)[CH2:11]4)=[O:3])[CH2:24]2)=[N:21][CH:22]=1

Participants

3

Reactant 2

HCID 552623565-Chloro-2-(pyrrolidin-3-YL)pyrimidineHCID 581714991-Hydroxy-4-adamantyl chloroformate

Product 1

HCID 498356441-Hydroxy-4-adamantyl 3-(5-chloropyrimidin-2-yl)pyrrolidine-1-carboxylate

Procedure

The title compound was prepared following a procedure analogous to that described in Example 19 Step 1 using 1-hydroxy-4-adamantyl chloroformate solution and 5-chloro-2-(pyrrolidin-3-yl)pyrimidine. Two isomers were separated by prep HPLC.

Workup

  1. customTwo isomers were separated by prep HPLC

Sources & evidence

ORD record
ord-3c164ad7eac44f93a60cd183bef885c8
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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