Ethylene Glycol → HCID 18186459, compound

HRID 1357521Notes

Reaction equation

[NH:1]([C:8]1[C:13]([CH2:14][O:15][CH2:16][CH3:17])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([OH:32])[CH2:28][N:29]([CH3:31])[CH3:30])=[CH:21][CH:20]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(O)C[OH:36]>>[NH:1]([C:8]1[C:13]([CH2:14][O:15][CH2:16][CH2:17][OH:36])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]([OH:32])[CH2:28][N:29]([CH3:31])[CH3:30])=[CH:23][CH:24]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 313Hydrochloric Acid

HCID 11774967HCID 11774967, compound

Product 1

HCID 18186459HCID 18186459, compound

Conditions

Temperature: 100 °C

Procedure

4-Anilino-5-(ethoxymethyl)-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}pyrimidine (Example 86, 70 mg, 0. 16 mmol) was dissolved in ethylene glycol (2 ml). Ethereal hydrogen chloride (1.0M; 0.32 ml, 0.32 mmol) was added, and the solution was heated at 100° C. for 20 hours. Volatile material was removed by evaporation and the residue was triturated with diethyl ether, giving the product as a dihydrochloride salt (43 mg). NMR (CDCl3): 2.34 (s, 6H), 2.3-2.6 (m, 2H), 3.63 (t, 2H), 3.73 (s, 1H), 3.86 (t, 2H), 3.96 (d, 2H), 4.08 (m, 1H), 4.54 (s, 2H), 6.86 (d, 2H), 6.88 (s, 1H), 7.08 (t, 1H), 7.30 (dd, 2H), 7.43 (d, 2H), 7.58 (d, 2H), 7.88 (m, 2H); MS (MH+): 454.3.

Workup

customVolatile material was removed by evaporation
customthe residue was triturated with diethyl ether

Sources & evidence

ORD record: ord-baf2da5f4890419285ca165188c63dac
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593326B1

Reaction notes

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