Hydrochloric Acid → 2,4-Diamino-6-ethyl-5-(3-(7-fluoro-2-methylquinolin-4-yloxy)propoxy)pyrimidine monohydrochloride

HRID 40810Notes

Reaction equation

HRID 40810 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][C:20]([F:24])=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:25])[CH:15]=2)=[C:4]([CH2:26][CH3:27])[N:3]=1.[ClH:28]>CO>[ClH:28].[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][C:20]([F:24])=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:25])[CH:15]=2)=[C:4]([CH2:26][CH3:27])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 252627632,4-Diamino-6-ethyl-5-(3-(7-fluoro-2-methylquinolin-4-yloxy)propoxy)pyrimidine

Product 1

HCID 685743112,4-Diamino-6-ethyl-5-(3-(7-fluoro-2-methylquinolin-4-yloxy)propoxy)pyrimidine monohydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring suspension of 2,4-diamino-6-ethyl-5-(3-(7-fluoro-2-methylquinolin-4-yloxy)propoxy)pyrimidine (0.3714 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 white crystalline solid (0.3834 g, 94%). m.p. >200° C., 1H NMR (400 MHz, DMSO-d6): 0.99 (3H, t, J=7.6 Hz), 2.35 (2H, m), 2.44 (2H, q, J=7.6 Hz), 2.64 (3H, s), 3.97 (2H, t, J=5.8 Hz), 4.45 (2H, t, J=5.5 Hz), 7.07 (1H, s), 7.45 (3H, m), 7.64 (1H, d, J=10.5 Hz), 7.90 (1H, bs), 8.19 (1H, dd, J=8.9, 6.3 Hz), 8.33 (1H, bs), 12.30 (1H, bs).

Workup

  1. customAfter evaporation of solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-88779991b4ac4525b7ae4347c4b345d4
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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