Ammonia → HCID 68506786, compound

HRID 2069464Notes

Reaction equation

[NH3:1].[OH:2][CH:3]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][CH:29]([CH3:31])[CH3:30])[N:22]=3)[O:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:4]OS(C)(=O)=O>CO>[NH2:1][CH2:4][CH:3]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]=[C:19]([C:21]3[CH:31]=[C:29]([CH3:30])[N:28]=[C:23]([NH:24][CH:25]([CH3:26])[CH3:27])[N:22]=3)[O:18][N:17]=2)=[CH:14][CH:15]=1)[OH:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 7M NH3 in methanol (35 mL) is added to methanesulfonic acid 2-hydroxy-2-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethyl ester (606 mg, 1.40 mmol, synthesis described for Example 143). The reaction mixture is stirred at 65° C. for 18 h and is then evaporated to give 293 mg of rac-2-amino-1-{4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol as a yellow oil; LC-MS: tR=0.73 min; [M+H]+=355.06.

Workup

customis then evaporated

Sources & evidence

ORD record: ord-e42d80c3cbc0492b84e468e2fe458adc
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299086B2

Reaction notes

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