Hydrochloric Acid → 5-(Aminomethyl)-4-(2-fluoro-2-propyl)pyrimidine Dihydrochloride

HRID 1749416Notes

Reaction equation

HRID 1749416 reaction equation
[F:1][C:2]([C:5]1[C:10]([CH2:11][NH:12]C(=O)OC(C)(C)C)=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])[CH3:3].[ClH:20]>C(Cl)Cl>[ClH:20].[ClH:20].[F:1][C:2]([C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123133695tert-Butyl ((4-(2-fluoropropan-2-yl)pyrimidin-5-yl)methyl)carbamate

Product 1

HCID 862229165-(Aminomethyl)-4-(2-fluoro-2-propyl)pyrimidine DihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((4-(2-fluoropropan-2-yl)pyrimidin-5-yl)methyl)carbamate (1.0 equiv.) was combined in DCM (1.5 M) at ambient temperature, and 4.0 M hydrogen chloride in dioxanes was added via syringe. The solution was allowed to stir at ambient temperature. After 16 h, the solution was condensed under reduced pressure to afford the title compound as a white solid (100% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.17 (d, J=1.56 Hz, 1H), 8.89 (s, 1H), 8.32 (br. s., 2H), 4.22 (dd, J=5.66, 3.32 Hz, 2H), 1.59-1.84 (m, 6H); MS(ESI) m/z [M+1]+.

Workup

  1. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-345e5536e6434844940c28c18bfcc382
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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