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

HRID 1876558Notes

Reaction equation

HRID 1876558 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

4

Reactant 2

HCID 1118Sulfuric AcidHCID 45378170Ds-7423

Product 1

HCID 547561685-{8-[(3R)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine sulfateYield 74.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-{8-[(3R)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine (101 mg, 0.194 mmol) in 10% aqueous ethanol solution (2 ml) was added 98% sulfuric acid (0.012 mL, 0.213 mmol) at room temperature, and the mixture was stirred for 30 minutes. The insoluble solid was collected and dried to give 5-{8-[(3R)-4-acetyl-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine sulfate (89 mg) as a yellow solid.

Workup

  1. customThe insoluble solid was collected
  2. customdried

Sources & evidence

ORD record
ord-8a60c6a43d81458fb3cab83c9b4f7725
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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