Hydrochloric Acid → 4-Piperazin-1-yl-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamine

HRID 1962209Notes

Reaction equation

HRID 1962209 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:24][CH2:23][O:22][CH2:21]3)[N:17]=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(O)=O.CO>[N:11]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:24][CH2:23][O:22][CH2:21]3)[N:17]=[C:16]([NH2:25])[N:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 670962764-[2-Amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 532577984-Piperazin-1-yl-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamineYield 68.8%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 4-[2-amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (600 mg, 1.72 mmol) in formic acid (10 mL) was treated with 6.0 N HCl (2 mL) and stirred for 2 h at rt. The mixture was diluted with MeOH (10 mL) and concentrated. This process was repeated twice, yielding 295 mg of a white solid as the hydrochloride salt. The crude material was chromatographed (2 M NH3 in MeOH/CH2Cl2) to afford 133 mg (50%) of the free base as an off-white solid. MS (ESI): mass calcd. for C12H19N5O, 249.1; m/z found, 250.2 [M+H]+. 1H NMR (CDCl3): 6.86 (s, 1H), 4.78 (br s, 2H), 3.98-4.07 (m, 2H), 3.83-3.90 (m, 2H), 3.54-3.58 (m, 4H), 3.22 (p, J=15.0, 7.3, 1H), 2.89-2.93 (m, 4H), 2.10-2.30 (m, 4H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-2809ad59f3b44d5eafdfec824bac63eb
Source dataset
uspto-grants-2013_04
Patent number
US08415366B2

Reaction notes

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