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

HRID 391067Notes

Reaction equation

HRID 391067 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(OC([NH:39][C:40]([CH3:45])([CH3:44])[C:41](O)=[O:42])=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[NH2:39][C:40]([CH3:45])([CH3:44])[C:41]([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:42]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 566486735-(7-Methyl-4-morpholino-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

Product 1

HCID 566487572-Amino-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-methylpropan-1-oneYield 80.3%

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 70 mg 2-(tert-butoxycarbonylamino)-2-methylpropanoic acid via General Procedure B, treated with TFA and purified via reverse phase HPLC to yield 71.3 mg of 352 after reverse phase HPLC purification. MS (Q1) 512.3 (M)+

Workup

  1. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-bdedc7bae3a24590b866e6558b01b015
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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