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

HRID 390818Notes

Reaction equation

HRID 390818 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[S:23][C:22]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)[N:13]=2)[CH2:4][CH2:3]1.C([NH:38][C@H:39]([C:41](O)=[O:42])[CH3:40])(OC(C)(C)C)=O>>[NH2:38][C@@H:39]([CH3:40])[C:41]([N:28]1[CH2:27][CH2:26][N:25]([CH2:24][C:22]2[S:23][C:9]3[C:8]([N:5]4[CH2:4][CH2:3][O:2][CH2:7][CH2:6]4)=[N:13][C:12]([C:14]4[CH:19]=[N:18][C:17]([NH2:20])=[N:16][CH:15]=4)=[N:11][C:10]=3[CH:21]=2)[CH2:30][CH2:29]1)=[O:42]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 85082Tert-butoxycarbonylalanineHCID 58234035HCID 58234035, compound

Product 1

HCID 58233860(S)-2-amino-1-(4-((2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propan-1-one

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 reacted with Boc-alanine via General Procedure B followed by Boc removal with TFA to generate 30.9 mg of 104 after purification. MS (Q1) 484.3 (M)+.

Workup

  1. customfollowed by Boc removal with TFA
  2. customafter purification

Sources & evidence

ORD record
ord-83054d83b3bc4ec29c514de6ae651203
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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