Methanol → HCID 90121193, compound

HRID 521732Notes

Reaction equation

HRID 521732 reaction equation
[F:1][C:2]1[C:3]([O:25][CH3:26])=[N:4][C:5]([N:9]2[CH2:17][CH:16]3[C:11]([C:19]4[CH:24]=[N:23][CH:22]=[CH:21][N:20]=4)([N:12]=[C:13]([NH2:18])[S:14][CH2:15]3)[CH2:10]2)=[N:6][C:7]=1[CH3:8].CO>C(=O)=O>[F:1][C:2]1[C:3]([O:25][CH3:26])=[N:4][C:5]([N:9]2[CH2:17][C@@H:16]3[C@@:11]([C:19]4[CH:24]=[N:23][CH:22]=[CH:21][N:20]=4)([N:12]=[C:13]([NH2:18])[S:14][CH2:15]3)[CH2:10]2)=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 90121194HCID 90121194, compound

Product 1

HCID 90121193HCID 90121193, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 280Carbon DioxideSolvent

Procedure

Racemic 6-(5-fluoro-4-methoxy-6-methyl-pyrimidin-2-yl)-7a-pyrazin-2-yl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-amine (490 mg, 1.3 mmol) is separated into its constituent enantiomers by chiral SFC (Column: Chiralcel OD-H (5μ), 21.2×250 mm; eluent: 50% methanol (0.2% diethylmethylamine) in CO2; flow: 70 mL/min at UV 260 nm). The first eluting isomer is the title compound (206 mg, 32%). ES/MS (m/e): 376 (M+1).

Sources & evidence

ORD record
ord-759645ba439841ed9f743dc1e498b5ec
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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