Dimethylamine → HCID 57636057, compound

HRID 2110649Notes

Reaction equation

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

Participants

Reactant 3

HCID 674Dimethylamine

HCID 887Methanol

HCID 57636044HCID 57636044, compound2×

Product 1

HCID 57636057HCID 57636057, compound

Procedure

A solution of [2-methanesulfonyl-6-(3-methoxy-phenyl)-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine [200 mg, 0.42 mmol, Intermediate (34) prepared as in Example 18, step 1] in a 2 M solution of dimethylamine in MeOH (2 mL, 4 mmol) is heated to 150° C. for 20 minutes in a Microwave. The mixture is concentrated, and the residue is subjected to chromatography on silica gel eluting with 70% EtOAc in heptane to afford 6-(3-methoxy-phenyl)-N*4*-[2-(4-methoxy-phenyl)-ethyl]-N*2*,N*2*-dimethyl-pyrimidine-2,4-diamine, which is treated with a solution of saturated hydrogen chloride in EtOAc (1 mL). The resulting precipitate is filtered and dried to afford 6-(3-methoxy-phenyl)-N*4*-[2-(4-methoxy-phenyl)-ethyl]-N*2*,N*2*-dimethyl-pyrimidine-2,4-diamine hydrochloride [0.11 g, 70%, Example 19] as a solid. LCMS: RT=2.85 minutes, MS: 379 (M+H). 1H NMR (300 MHz, CD3OD), □7.46 (1H, t, J=8.1 Hz), 7.26-7.1 (5H, m), 6.83 (2H, d, J=8.1 Hz), 6.27 (1H, s), 4.85 (1H, brs), 3.87 (3H, s), 3.74 (3H, s), 3.71 (2H, t, J=7.2 Hz), 3.28 (6H, s), 2.89 (2H, t, J=7.2 Hz). IC50=4652 nM

Workup

concentrationThe mixture is concentrated

Sources & evidence

ORD record: ord-2ecc8e3443b048509c6451210d89424d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517889B2

Reaction notes

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