Hydrochloric Acid → HCID 67312844, compound

HRID 1012175Notes

Reaction equation

HRID 1012175 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][CH:12]=1)(C)(C)C.[ClH:28].C(O)(C(F)(F)F)=O>O1CCOCC1.C(Cl)Cl>[ClH:28].[NH2:7][C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 59468607HCID 59468607, compound

Product 1

HCID 67312844HCID 67312844, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

[5-(2-m-Tolylamino-pyrimidin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester was treated with 4 N HCl in 1,4-dioxane for 6 hours or 20% TFA in DCM for 2 hours. The solution was dried in vacuo to afford [4-(5-aminothiophen-2-yl)-pyrimidin-2-yl]-m-tolyl-amine HCl salt. The amine salt was also neutralized by drying down the HCl/dioxane solution, redissolving in EtOAc and washing with saturated NaHCO3 (2×) and brine (1×) and dried over Na2SO4. Concentrated and redissolved and dried down 2× from DCM to obtain an orange foam [4-(5-aminothiophen-2-yl)-pyrimidin-2-yl]-m-tolyl-amine (quantitative). MS: m/z 283 (M+H+).

Workup

  1. customThe solution was dried in vacuo

Sources & evidence

ORD record
ord-e5da64b5e98348ffbd2251413bf29ac8
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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