Ammonium Hydroxide → (1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol

HRID 526996Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:16][CH2:15][CH2:14][C@:11]3([O:13][CH2:12]3)[CH2:10]2)[C:5]([F:17])=[CH:4][N:3]=1.[OH-].[NH4+:19]>O>[NH2:19][CH2:12][C@:11]1([OH:13])[CH2:14][CH2:15][CH2:16][C@H:9]([NH:8][C:6]2[C:5]([F:17])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Chloro-5-fluoro-N-[(3S,5S)-1-oxaspiro[2.5]octan-5-yl]pyrimidin-4-amine, 46a, (0.19 g, 0.73 mmol) was dissolved in water (75 mL) and treated with 30% ammonium hydroxide (10 mL, 86.0 mmol). The suspension was heated to 50° C. for 5 hrs then allowed to stir at room temperature overnight. The volatiles were evaporated under reduced pressure, and the residue, (1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoro-pyrimidin-4-ylamino)cyclohexanol, was taken into the next step without further purification.

Workup

customThe volatiles were evaporated under reduced pressure
customthe residue, (1S,3S)-1-(aminomethyl)-3-(2-chloro-5-fluoro-pyrimidin-4-ylamino)cyclohexanol, was taken into the next step without further purification

Sources & evidence

ORD record: ord-2404dc46f95646038bd58d755d8d7ae5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345708B2

Reaction notes

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