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

HRID 40804Notes

Reaction equation

HRID 40804 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]=[C:21]([F:24])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1.[ClH:27]>CO>[ClH:27].[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]=[C:21]([F:24])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[C:4]([CH2:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25227491HCID 25227491, compound

Product 1

HCID 685770732,4-Diamino-6-ethyl-5-(3-(6-fluoroquinolin-4-yloxy)propoxy)pyrimidine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,4-diamino-6-ethyl-5-(3-(6-fluoroquinolin-4-yloxy)propoxy)pyrimidine (10.02 g, 28 mmol) in methanol (40 mL) was added 5.3 mL of concentrated HCl. The titled compound precipitated almost immediately and was obtained as a white crystalline solid after suction filtration followed by washing with acetone and air-dried (11.81 g, 98%, m.p. 212-214° C.). 1H NMR (400 MHz, DMSO-d6): 1.05 (3H, t, J=7.4 Hz), 2.40 (2H, m), 2.48 (2H, m), 3.98 (2H, t, J=5.8 Hz), 4.68 (2H, t, J=5.5 Hz), 7.50 (bs, 2H), 7.60 (1H, d, J=6.5 Hz), 7.90 (1H, s), 8.04 (1H, dt, J=9.0, 2.6 Hz), 8.10 (1H, dd, J=8.9, 2.3 Hz), 8.33 (1H, s), 8.43 (1H, dd, J=9.3, 4.8 Hz), 9.17 (1H, d, J=6.4 Hz), 12.70 (1H, s).

Workup

  1. customThe titled compound precipitated almost immediately
  2. customwas obtained as a white crystalline solid
  3. filtrationafter suction filtration
  4. washby washing with acetone
  5. customair-dried (11.81 g, 98%, m.p. 212-214° C.)

Sources & evidence

ORD record
ord-064840ed9e5840418937556be1917095
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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