1-(2-Hydroxyethyl)piperazine → 2-(4-(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)piperazin-1-yl)ethanol

HRID 1365813Notes

Reaction equation

HRID 1365813 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9](S(C)(=O)=O)=[N:8][C:6]=2[N:7]=1.[N:21]1([CH2:27][CH2:28][OH:29])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([N:24]3[CH2:25][CH2:26][N:21]([CH2:27][CH2:28][OH:29])[CH2:22][CH2:23]3)=[N:8][C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 576854065-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine

Product 1

HCID 866300782-(4-(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)piperazin-1-yl)ethanol

Procedure

5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine was reacted with 2-(piperazin-1-yl)ethanol, via General Procedure C, to give crude 2-(4-(5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)piperazin-1-yl)ethanol, which was then reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure C again to give 134 after purification by reverse HPLC. MS (Q1) 444 (M+)

Sources & evidence

ORD record
ord-a173f25bea234c52b03e5a9854205faa
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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