Hydrochloric Acid → 4-chloro-6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine bis-hydrochloride

HRID 2375861Notes

Reaction equation

HRID 2375861 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([Cl:22])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:24].O1CCOCC1>>[ClH:22].[ClH:24].[Cl:22][C:21]1[C:16]2[CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[NH:23][C:17]=2[N:18]=[CH:19][N:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 866078174-chloro-6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine bis-hydrochloride

Procedure

To 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (601.6 mg, 1.797 mmol, 1 eq), a 4.0 M solution of HCl in 1,4-dioxane (15 mL, 33 eq) was added and the reaction was stirred at rt for 18 h. The solid was then filtered off, washed several times with ether, and dried under vacuum pressure, yielding the title compound as a yellow solid. 1H NMR (400 MHz, DMSOd6): δ=2.77 (s, 2H), 3.33 (d, J=4.8 Hz, 2H), 3.83 (s, br, 2H), 5.27-5.65 (s, br, —NH+H2O), 6.60 (s, 1H), 6.71 (d, J=1.6 Hz, 1H), 8.59 (s, 1H), 9.30 (s, br, —NH), 12.85 (s, H+). MS (ES+): m/z 235.09/237.11 (3) [MH+]; 206.12/208.14 (100) [MH+—CH3N). HPLC: tR=1.52 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe solid was then filtered off
  2. washwashed several times with ether
  3. customdried under vacuum pressure

Sources & evidence

ORD record
ord-e9bb78765d414896a9fda93ad060c7e8
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…