Hydrochloric Acid → (S)-2-amino-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propan-1-one

HRID 391069Notes

Reaction equation

HRID 391069 reaction equation
Cl.[CH3:2][C:3]1[C:7]2[N:8]=[C:9]([C:18]3[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)[N:10]=[C:11]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:6]=2[S:5][C:4]=1[CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C([NH:39][C@H:40]([C:42](O)=[O:43])[CH3:41])(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>>[NH2:39][C@@H:40]([CH3:41])[C:42]([N:29]1[CH2:30][CH2:31][N:26]([CH2:25][C:4]2[S:5][C:6]3[C:11]([N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)=[N:10][C:9]([C:18]4[CH:19]=[N:20][C:21]([NH2:24])=[N:22][CH:23]=4)=[N:8][C:7]=3[C:3]=2[CH3:2])[CH2:27][CH2:28]1)=[O:43]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 85082Tert-butoxycarbonylalanineHCID 566486735-(7-Methyl-4-morpholino-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Product 1

HCID 56648677(S)-2-amino-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propan-1-oneYield 61%

Procedure

Crude HCl salt of 5-(7-methyl-4-morpholino-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine (74 mg) was reacted with 60 mg Boc-L-Alanine via General Procedure B, treated with TFA and purified via reverse phase HPLC to yield 52.7 mg of 354 after reverse phase HPLC purification. MS (Q1) 498.3 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-72aa3715d99449babeef8fc07c9d980e
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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