Hydrochloric Acid → 4-(2-Methoxy-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1B(O)O.[Cl:16][C:17]1[C:18]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][C:19]=2[N:20]=[CH:21][N:22]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCOCC1.O.C(Cl)Cl.CCOCC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[ClH:16].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:17]1[C:18]2[CH2:26][CH2:25][NH:24][CH2:23][C:19]=2[N:20]=[CH:21][N:22]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Procedure
A solution of PdCl2(dppf)-CH2Cl2 adduct (0.091 g, 0.111 mmol), (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid (0.815 g, 3.71 mmol), tert-butyl 4-chloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (1.000 g, 3.71 mmol), and potassium carbonate (2.050 g, 14.83 mmol) in 12 mL of dioxane and 4 mL water was heated to 110° C. for one hour. The reaction mixture was then diluted with DCM, the organics were dried over MgSO4 and concentrated. The crude residue was treated with HCl (4N in dioxane) (9.27 ml, 37.1 mmol) and was allowed to stir at room temperature overnight. The reaction mixture was diluted with ether, and the resulting solids were filtered off and dried yielding 4-(2-methoxy-4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine hydrochloride (1.333 g, 3.86 mmol, 104% yield) as a gray solid with minor impurities. (M+H)+=310.2.
Workup
- dry with materialthe organics were dried over MgSO4
- concentrationconcentrated
- filtrationthe resulting solids were filtered off
- customdried
Sources & evidence
- ORD record
- ord-60952c7f7835494e8ef7be51ffe45a73
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051311B2
Reaction notes
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