Hydrochloric Acid → (R)-(1(4,5-Diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

HRID 931060Notes

Reaction equation

HRID 931060 reaction equation
[ClH:1].[NH2:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][N:6]=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH2:13]2)[N:4]=1>CO.[Pd]>[ClH:1].[ClH:1].[NH2:2][C:3]1[C:8]([NH2:9])=[CH:7][N:6]=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH2:13]2)[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89854015Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl-

Product 1

HCID 89853293(R)-(1(4,5-Diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (470 μL, 37 wt % aq) was added to a solution of (R)-(1-(4-amino-5-nitropyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (380 mg, 1.13 mmol) in methanol (30 mL). The solution was hydrogenated using the H-Cube (10% Pd/C, full H2, 18° C., 1 mL/min). A second cycle was run using the same conditions. The solvent was removed under reduced pressure and the residue was co-evaporated with toluene several times to afford the title compound as a yellow solid (405 mg). The material was used without further purification. 1H NMR (CD3OD) δ 1.68 (d, 1H), 1.81 (d, 1H), 1.91 (quin, 3H), 1.96-2.09 (m, 3H), 2.84 (t, 1H), 3.34-3.47 (m, 4H), 3.52-3.59 (m, 1H), 3.61-3.70 (m, 1H), 4.32 (d, 1H), 4.17 (d, 1H), 7.70 (s, 1H); MS (ES+) (M+H) 291.2.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-306dd1f308154e02b0086a2dd90141ca
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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