Hydrochloric Acid → HCID 68576455, compound

HRID 40807Notes

Reaction equation

HRID 40807 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:24])[CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1.[ClH:27]>CO>[ClH:27].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:24])[CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25262922HCID 25262922, compound

Product 1

HCID 68576455HCID 68576455, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring suspension of 2,4-diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidine (0.353 g, 1 mmol) in methanol (10 mL) was added one equivalent of hydrochloric acid at 25° C. After evaporation of solvent and trituration with diethyl ether, product was obtained as light yellow solid (0.3587 g, 92%). mp: 194-196° C. (dec.). 1H NMR (400 MHz, DMSO-d6): 0.99 (3H, t, J=7.5 Hz), 2.36 (2H, m), 2.44 (2H, q, J=7.5 Hz), 2.65 (3H, s), 3.97 (2H, t, J=6.0 Hz), 4.45 (2H, t, J=5.6 Hz), 7.09 (1H, s), 7.40 (2H, bs), 7.54 (2H, t, J=7.5 Hz), 7.75 (1H, t, J=7.8 Hz), 7.93 (2H, m), 8.14 (2H, m), 12.55 (1H, bs).

Workup

  1. customAfter evaporation of solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-cf1d8972e30b4d8cb6f938162f4f101f
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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