Hydrochloric Acid → 2-phenyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine hydrochloride

HRID 984898Notes

Reaction equation

HRID 984898 reaction equation
C(OC([N:8]1[CH2:23][CH2:22][C:11]2[N:12]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[CH:15][C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:24]>C(OCC)(=O)C>[ClH:24].[C:16]1([C:13]2[N:14]=[CH:15][C:10]3[CH2:9][NH:8][CH2:23][CH2:22][C:11]=3[N:12]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53946157tert-Butyl 2-phenyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Product 1

HCID 223286342-phenyl-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-phenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester (prepared according to the method of Example 101, Step C, 304 mg, 0.98 mmol) in ethyl acetate (2 mL) was added hydrogen chloride (2.5 M in ethyl acetate, 3.9 mL, 9.76 mmol). This mixture was stirred at room temperature for 16 h and concentrated to give 256 mg (>100%) of the title compound of Example 101, Step D as a pale yellow solid. 1H NMR (CD3OD, 400 MHz) δ 8.75 (s, 1H), 8.42-8.38 (c, 2H), 7.51-7.45 (c, 3H), 4.48 (s, 2H), 3.68 (t, 2H) 3.35-3.25 (buried, 2H); MS (APCI) 212 (MH+).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-09cf8555005c4d7cb4e982de29313bda
Source dataset
uspto-grants-2005_03
Patent number
US06869943B2

Reaction notes

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