Hydrochloric Acid → N-[(1R)-1-Phenylethyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 38520Notes

Reaction equation

[C:1]1([C@H:7]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>CC(O)C.C(OCC)(=O)C>[C:1]1([C@H:7]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][NH:21][CH2:22][C:17]=4[S:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-{[(1R)-1-phenylethyl]amino}-5,8-dihydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate from Example 17A (413 mg, 1.00 mmol) was dissolved in 2-propanol (4 mL), and 4 M gaseous hydrogen chloride in dioxane (0.5 mL, 2 mmol) was added. The mixture was heated to 80° C. for 3 h. Further hydrogen chloride solution (0.5 mL) was added, and the mixture was heated to 80° C. for further 30 min. Subsequently, the solution was diluted with ethyl acetate, washed with satd. aqueous sodium carbonate solution, dried over sodium sulfate, and the solvent was removed in vacuo. The product was purified by column chromatography on silica gel (eluent: DCM/MeOH 10:1) to yield 244 mg (78%) of the title compound.

Workup

temperaturethe mixture was heated to 80° C. for further 30 min
washwashed with satd
dry with materialaqueous sodium carbonate solution, dried over sodium sulfate
customthe solvent was removed in vacuo
customThe product was purified by column chromatography on silica gel (eluent: DCM/MeOH 10:1)

Sources & evidence

ORD record: ord-274ee01194704ecf9cfbb33beb67ab17
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

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