Hydrochloric Acid → (s)-1-(4-((2-(2-(Dimethylamino)pyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one

HRID 391124Notes

Reaction equation

HRID 391124 reaction equation
ClC1N=C(N2CCOCC2)C2SC(CN3CCN(C(OC(C)(C)C)=O)CC3)=C(C)C=2N=1.Cl.[CH3:33][N:34]([CH3:64])[C:35]1[N:40]=[CH:39][C:38]([C:41]2[N:42]=[C:43]([N:58]3[CH2:63][CH2:62][O:61][CH2:60][CH2:59]3)[C:44]3[S:49][C:48]([CH2:50][N:51]4[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]4)=[C:47]([CH3:57])[C:45]=3[N:46]=2)=[CH:37][N:36]=1.[C:65](O)(=[O:69])[C@H:66]([CH3:68])[OH:67]>>[CH3:64][N:34]([CH3:33])[C:35]1[N:40]=[CH:39][C:38]([C:41]2[N:42]=[C:43]([N:58]3[CH2:59][CH2:60][O:61][CH2:62][CH2:63]3)[C:44]3[S:49][C:48]([CH2:50][N:51]4[CH2:56][CH2:55][N:54]([C:65](=[O:69])[C@@H:66]([OH:67])[CH3:68])[CH2:53][CH2:52]4)=[C:47]([CH3:57])[C:45]=3[N:46]=2)=[CH:37][N:36]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 107689L-Lactic AcidHCID 56648760Tert-butyl 4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylateHCID 66934145n,n-Dimethyl-5-(7-methyl-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Product 1

HCID 24948737(s)-1-(4-((2-(2-(Dimethylamino)pyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one

Procedure

Tert-butyl 4-((2-chloro-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate (100 mg) was reacted with 70 mg 2-(dimethylamino)pyrimidin-5-yl-5-boronic pinacol ester via General Procedure A. This crude intermediate was subjected to General Procedure D in which 100 mg of the crude HCl salt of N,N-dimethyl-5-(7-methyl-4-morpholino-6-((piperazin-1-yl)methyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine was reacted with 60 mg L-lactic Acid via General Procedure B to give 25.5 mg of 407 after reverse phase HPLC purification. MS (Q1) 527.3 (M)+.

Sources & evidence

ORD record
ord-1442797305244433b3b1f08e9f8a6c8f
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

Loading…