Hydrochloric Acid → 2,4-Diamino-6-ethyl-5-(3-(quinolin-4-yloxy)propoxy)pyrimidine dihydrochloride

HRID 40800Notes

Reaction equation

HRID 40800 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]=[CH:16][CH:15]=2)=[C:4]([CH2:24][CH3:25])[N:3]=1.[ClH:26]>CO>[ClH:26].[ClH:26].[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]=[CH:16][CH:15]=2)=[C:4]([CH2:24][CH3:25])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 252629242,4-Diamino-6-ethyl-5-(3-(quinolin-4-yloxy)propoxy)pyrimidine

Product 1

HCID 685745602,4-Diamino-6-ethyl-5-(3-(quinolin-4-yloxy)propoxy)pyrimidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-diamino-6-ethyl-5-(3-(quinolin-4-yloxy)propoxy)pyrimidine (0.1740 g, 0.51 mmol) was suspended in methanol (1 mL) and 2 equivalents of concentrated HCl was added. The titled compound was obtained, after evaporation and trituration of the residue with acetonitrile, as an off-white crystalline solid (0.2004 g, 95%). 1H NMR (400 MHz, DMSO-d6): 1.04 (3H, t, J=7.6 Hz), 2.42 (2H, m), 2.45 (2H, t, J=7.0 Hz), 3.97 (2H, t, J=5.9 Hz), 4.72 (2H, t, J=5.9 Hz), 7.56 (2H, bs), 7.61 (1H, d, J=6.7 Hz), 7.87 (1H, t, J=7.8 Hz), 7.97 (1H, s), 8.11 (1H, ddd, J=1.0, 7.3, 8.2 Hz), 8.35-8.40 (3H, m), 9.18 (1H, d, J=6.6 Hz), 12.86 (1H, s).

Sources & evidence

ORD record
ord-53b1de3154644f968b6988608816223d
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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