tert-butyl N-(4-[[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy]cyclohexyl)carbamate → 4-[[6-(Propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy]cyclohexan-1-amine

HRID 525071Notes

Reaction equation

[CH3:1][CH:2]([C:4]1[S:27][C:7]2[N:8]=[CH:9][N:10]=[C:11]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([NH:19]C(=O)OC(C)(C)C)[CH2:15][CH2:14]3)[C:6]=2[CH:5]=1)[CH3:3]>ClCCl>[CH3:3][CH:2]([C:4]1[S:27][C:7]2[N:8]=[CH:9][N:10]=[C:11]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]3)[C:6]=2[CH:5]=1)[CH3:1]

Participants

Conditions

Temperature: 5 °C

Procedure

To a 100-mL round-bottom flask was added a solution of tert-butyl N-(4-[[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy]cyclohexyl)carbamate (4.8 g, 12.26 mmol, 1.00 equiv) in dichloromethane (100 mL). Hydrogen chloride was bubbled through the solution. The resulting solution was stirred for 5 h at 0-10° C. The resulting mixture was concentrated under vacuum. This resulted in 3.6 g (90%) of 4-[[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy]cyclohexan-1-amine hydrochloride as a yellow solid. MS: m/z 292 (M+H)+.

Workup

customHydrogen chloride was bubbled through the solution
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 3.6 g (90%) of 4-[[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy]cyclohexan-1-amine hydrochloride as a yellow solid

Sources & evidence

ORD record: ord-224b81fdab06408586b1831afdcdd1da
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340554B2

Reaction notes

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