2-Methanesulfonylacetic acid → 1-(4-((2-(2-Aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)ethanone

HRID 881242Notes

Reaction equation

HRID 881242 reaction equation
ClC1N=C(N2CCOCC2)C2SC(CN3CCN(C(OC(C)(C)C)=O)CC3)=CC=2N=1.[O:31]1[CH2:36][CH2:35][N:34]([C:37]2[C:38]3[S:52][C:51]([CH2:53][N:54]4[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]4)=[CH:50][C:39]=3[N:40]=[C:41]([C:43]3[CH:44]=[N:45][C:46]([NH2:49])=[N:47][CH:48]=3)[N:42]=2)[CH2:33][CH2:32]1.[CH3:60][S:61]([CH2:64][C:65](O)=[O:66])(=[O:63])=[O:62]>>[NH2:49][C:46]1[N:47]=[CH:48][C:43]([C:41]2[N:42]=[C:37]([N:34]3[CH2:33][CH2:32][O:31][CH2:36][CH2:35]3)[C:38]3[S:52][C:51]([CH2:53][N:54]4[CH2:55][CH2:56][N:57]([C:65](=[O:66])[CH2:64][S:61]([CH3:60])(=[O:63])=[O:62])[CH2:58][CH2:59]4)=[CH:50][C:39]=3[N:40]=2)=[CH:44][N:45]=1

Participants

4

Reactant 3

HCID 37328412-Methanesulfonylacetic acidHCID 57494058Tert-butyl 4-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylateHCID 58234035HCID 58234035, compound

Product 1

HCID 248127701-(4-((2-(2-Aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-(methylsulfonyl)ethanone

Procedure

The HCl salt of 5-(4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine (100 mg) was then reacted with methanesulfonylacetic acid via General Procedure B to generate 56 mg of 101. MS (Q1) 533.2 (M)+.

Sources & evidence

ORD record
ord-612774ff7a4e4ee9b5ee5917cb37d17a
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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