Hydrochloric Acid → (4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine hydrochloride

HRID 470283Notes

Reaction equation

HRID 470283 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:17][C@@H:16]3[C@@:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([N:12]=[C:13]([NH2:18])[S:14][CH2:15]3)[CH2:10]2)=[N:7][CH:8]=1>C(OCC)(=O)C>[ClH:1].[F:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH2:17][C@@H:16]3[C@@:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([N:12]=[C:13]([NH2:18])[S:14][CH2:15]3)[CH2:10]2)=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 78318759(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine

Product 1

HCID 78318758(4aR,7aS)-6-(5-Fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of hydrogen chloride (1 M in diethyl ether) (17 mL, 17 mmol) is added to a solution of (4aR,7aS)-6-(5-fluoropyrimidin-2-yl)-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (4.6 g, 14 mmol) in ethyl acetate (46 mL) and stirred for one hour. The solvent is removed under vacuum to give the title compound (5 g, 98%). ES/MS (m/e): 330 (M+H).

Workup

  1. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-950591dc5c094c558750d4da1f695c20
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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