Hydrochloric Acid → HCID 58234007, compound

HRID 881316Notes

Reaction equation

HRID 881316 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[CH:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.C(N1CCNCC1)(OC(C)(C)C)=O.ClC1N=C(N2CCOCC2)C2C=C(CN3CCN(C(OC(C)(C)C)=O)CC3)SC=2N=1.Cl.ClC1N=C(N2CCOCC2)C2C=C(CN3CCNCC3)SC=2N=1.C(O)(=O)CO.ClC1N=C(N2CCOCC2)C2C=C(C[N:102]3[CH2:107][CH2:106][N:105]([C:108](=[O:111])[CH2:109][OH:110])[CH2:104][CH2:103]3)SC=2N=1.CC1(C)C(C)(C)OB([C:126]2[CH:127]=[N:128][C:129]([NH2:132])=[N:130][CH:131]=2)O1>>[NH2:132][C:129]1[N:130]=[CH:131][C:126]([C:2]2[N:3]=[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:5]3[CH:10]=[C:9]([CH2:11][N:102]4[CH2:103][CH2:104][N:105]([C:108](=[O:111])[CH2:109][OH:110])[CH2:106][CH2:107]4)[S:8][C:6]=3[N:7]=2)=[CH:127][N:128]=1

Participants

9

Reactant 8

HCID 313Hydrochloric AcidHCID 757Glycolic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 568338442-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehydeHCID 56833847HCID 56833847, compound2×HCID 56833848HCID 56833848, compound2×HCID 86623520HCID 86623520, compound2×

Product 1

HCID 58234007HCID 58234007, compound

Procedure

2-Chloro-4-morpholinothieno[2,3-d]pyrimidine-6-carbaldehyde from General Procedure D-2 (720 mg) was reacted with Boc-piperazine via General Procedure B-4 to generate tert-butyl 4-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate. Tert-butyl 4-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperazine-1-carboxylate (1.1 g) was converted via General Procedure D to the HCl salt of 2-chloro-4-morpholino-6-((piperazin-1-yl)methyl)thieno[2,3-d]pyrimidine. 2-Chloro-4-morpholino-6-((piperazin-1-yl)methyl)thieno[2,3-d]pyrimidine (600 mg) was reacted with glycolic acid via General Procedure B to 1-(4-((2-chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxyethanone. 1-(4-((2-Chloro-4-morpholinothieno[2,3-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxyethanone (265 mg) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine via General Procedure A to give 180. MS (Q1) 471.2 (M)+.

Sources & evidence

ORD record
ord-b6f3fcc05c0a4b37985791aaf8631bce
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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