Triethylamine → 5-chloro-N-(2-(methylsulfonyl)ethyl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine

HRID 1365812Notes

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.[CH3:21][S:22]([CH2:25][CH2:26][NH2:27])(=[O:24])=[O:23].C(N(CC)CC)C>>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[C:5]2[S:10][C:9]([NH:27][CH2:26][CH2:25][S:22]([CH3:21])(=[O:24])=[O:23])=[N:8][C:6]=2[N:7]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 43405612-(Methylsulfonyl)ethanamine

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

Product 1

HCID 866300775-chloro-N-(2-(methylsulfonyl)ethyl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine

Procedure

5-Chloro-2-(methylsulfonyl)-7-morpholinothiazolo[4,5-d]pyrimidine was reacted with 2-(methylsulfonyl)ethanamine (HCl salt), using 2.8 equiv of triethylamine, via General Procedure C, to give crude 5-chloro-N-(2-(methylsulfonyl)ethyl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine, 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 133 after purification by reverse HPLC. MS (Q1) 437 (M+)

Sources & evidence

ORD record: ord-2520ca77b56c43cd8e33fa269189d522
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893059B2

Reaction notes

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