Sulfuric Acid → 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine sulfate

HRID 421372Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([CH2:32][C:33]([F:36])([F:35])[F:34])[C:12]3[C:17]([N:18]=2)=[C:16]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:15]=[C:14]([C:25]2[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)[N:13]=3)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2].[S:38](=[O:42])(=[O:41])([OH:40])[OH:39]>C(O)C>[S:38]([OH:42])([OH:41])(=[O:40])=[O:39].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]([CH2:32][C:33]([F:36])([F:35])[F:34])[C:12]3[C:17]([N:18]=2)=[C:16]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[N:15]=[C:14]([C:25]2[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)[N:13]=3)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (48.7 mg, 0.09 mmol) in 10% aqueous ethanol solution (1 ml) was added 98% sulfuric acid (5.44 μL, 0.09 mmol) at room temperature, and the mixture was heated up to 50° C., then allowed to be cooled down to r.t., and stirred for 5 hr. The solid precipitated out was collected and dried to give 5-{8-[(3S)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine sulfate (48.9 mg) as a yellow solid.

Workup

temperatureto be cooled down to r.t.
customThe solid precipitated out
customwas collected
customdried

Sources & evidence

ORD record: ord-a7513cfd8fa645b59e074dae3e421c9d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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