Hydrochloric Acid → 5-(3-aminopyrrolidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride

HRID 1410100Notes

Reaction equation

HRID 1410100 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([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)=[N: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:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[N:7]=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 68379621Tert-butyl 1-(7-(5,6-dimethoxypyridin-2-ylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 683793615-(3-aminopyrrolidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 1-(7-(5,6-dimethoxypyridin-2-ylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamate (260 mg, 0.549 mmol) in 20 mL of saturated HCl in dioxane was stirred at room temperature for 24 hours. The solvent was evaporated to give 5-(3-aminopyrrolidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (283 mg, crude) as a yellow solid. It was used directly in the next step without further purification. LC-MS: 187.6 [M/2+H]+, 374.0 [M+H]+, tR=1.18 min.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a4e3512ad61d4ed1a9d13c18f8a2d09b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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