Hydrochloric Acid → 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride

HRID 1410004Notes

Reaction equation

HRID 1410004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:33]=[CH:32][S:31][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[ClH:34]>O1CCOCC1>[ClH:34].[NH2:23][CH:20]1[CH2:21][CH2:22][N:18]([C:16]2[N:17]=[C:12]([NH:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[C:13]3[N:33]=[CH:32][S:31][C:14]=3[N:15]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68379471Tert-butyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 683792715-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamate (191 mg, 0.40 mmol) in 50 mL of saturated HCl in dioxane was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure to give 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (165 mg, 100%) as a solid. This was used directly in the next step without further purification. LC-MS: 373.1 [M+H]+, tR=1.15 min.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8232131591f4eb59d7e4d7f369e9f4b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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