Hydrochloric Acid → HCID 69062473, compound

HRID 2110642Notes

Reaction equation

HRID 2110642 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:4]=1.[ClH:27]>CCOC(C)=O>[ClH:27].[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57636039HCID 57636039, compound

Product 1

HCID 69062473HCID 69062473, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-{2-Methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenol [0.3 g, Example 35(p)] in EtOAc is added a saturated solution of hydrogen chloride in EtOAc (3 mL) and the resulting precipitate is filtered, and dried to afford 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenol hydrochloride [0.31 g, Example 15(a)] as a solid. LCMS: RT=2.55 minutes, MS: 352 (M+H). 1H NMR [(CD3)2SO]: δ 10.1 (1H, brs), 9.6 (1H, brs), 7.64-7.54 (1H, m), 7.34 (1H, t, J=8.1 Hz), 7.21-7.12 (4H, m), 7.02 (1H, d, J=7.5 Hz), 6.85 (2H, d, J=8.4 Hz), 6.67 (1H, s), 4.06 (3H, s), 3.71 (3H, s), 3.7-3.6 (2H, m), 2.85 (2H, t, J=7.2 Hz). IC50=0.1 nM

Workup

  1. filtrationthe resulting precipitate is filtered
  2. customdried

Sources & evidence

ORD record
ord-dbee2f64266343b0aed88fef5be9d759
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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