Hydrochloric Acid → HCID 67370188, compound

HRID 72800Notes

Reaction equation

HRID 72800 reaction equation
C(OC([N:8]1[CH2:30][CH2:29][C:11]2[N:12]=[C:13]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH3:28])[N:14]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:31]>CCOCC.O1CCOCC1>[ClH:31].[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]2[C:10]3[CH2:9][NH:8][CH2:30][CH2:29][C:11]=3[N:12]=[C:13]([N:23]3[CH2:27][CH2:26][CH2:25][CH:24]3[CH3:28])[N:14]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67367913HCID 67367913, compound

Product 1

HCID 67370188HCID 67370188, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester (0.193 g, 0.47 mmol) in Et2O (2 mL) was added 4 M HCl in dioxane (2.5 mL). After 16 h, the mixture was concentrated and the residue was triturated with Et2O to give the title compound (0.124 g, 76%) as a white solid. MS (ESI): mass calcd. for C18H21FN4, 312.4; m/z found, 313.4 [M+H]+. 1H NMR (DMSO-d6): 9.54 (m, 2H), 7.64 (dd, J=8.5, 5.5, 2H), 7.37 (t, J=8.8, 2H), 4.23-4.04 (m, 3H), 3.58-3.36 (m, 4H), 3.03-2.95 (m, 2H), 2.08-1.96 (m, 2H), 1.93-1.85 (m, 1H), 1.71-1.64 (m, 1H), 1.21 (d, J=6.3, 3H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-4ff3fa606f854ebb927e8a120d050e35
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

Loading…