2-Methoxyethanol → HCID 86666888, compound

HRID 510973Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([C:12]2[N:17]=[C:16]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH:15]=[CH:14][CH:13]=2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)[CH3:3].Cl[C:26]1[N:34]=[CH:33][N:32]=[C:31]2[C:27]=1[N:28]=[CH:29][N:30]2[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1.COCCO.CCN(C(C)C)C(C)C>>[Cl:10][C:8]1[C:7]([CH3:11])=[C:6]([C:12]2[N:17]=[C:16]([C:18]([N:20]([CH3:21])[CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=2)[C:5]([O:23][CH3:24])=[C:4]([CH:2]([NH:1][C:26]2[N:34]=[CH:33][N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][N:30]3[CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH3:3])[CH:9]=1

Participants

Reactant 4

HCID 80192-Methoxyethanol

HCID 81531Diisopropylethylamine

HCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HCID 86666885HCID 86666885, compound

Product 1

HCID 86666888HCID 86666888, compound

Conditions

Temperature: 105 °C

Procedure

The 6-{3-[1-aminoethyl]-5-chloro-2-methoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (0.025 g, 0.072 mmol) was combined with 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (0.022 g, 0.14 mmol, from Example 176, Step 4) in 2-methoxyethanol (1.0 mL, 13 mmol) and DIPEA (0.037 g, 0.29 mmol) in a sealed tube. The reaction was heated to 105° C. in an oil bath for 18 hours. Without workup, the reaction was carried into the next step.

Sources & evidence

ORD record: ord-16c47aca3e9d4ce9841840f67087a38d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096600B2

Reaction notes

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