Sodium Bicarbonate → HCID 66917515, compound

HRID 506869Notes

Reaction equation

Cl.N1C=CC=CC=1.C[O:9][C:10]1[C:15](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[CH:14][C:13]([C:37]2[CH:42]=[CH:41][N:40]=[C:39]([NH:43][CH3:44])[N:38]=2)=[CH:12][N:11]=1.C(=O)(O)[O-].[Na+]>CO>[N:24]1([C:21]2[CH:20]=[CH:19][C:18]([CH:17]=[CH:16][C:15]3[C:10](=[O:9])[NH:11][CH:12]=[C:13]([C:37]4[CH:42]=[CH:41][N:40]=[C:39]([NH:43][CH3:44])[N:38]=4)[CH:14]=3)=[CH:23][CH:22]=2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1

Participants

Conditions

Temperature: 150 °C

Procedure

Pyridine hydrochloride (2 g) was added to tert-butyl 4-(4-((E)-2-(2-methoxy-5-(2-(methylamino)pyrimidin-4-yl)pyridin-3-yl)vinyl)phenyl)piperazine-1-carboxylate (168 mg, 0.33 mmol) and the mixture was heated at 150° C. for 30 min. The reaction mixture was dissolved in MeOH (30 mL) and solid sodium bicarbonate was added until bubbling ceased. The suspension was filtered and the filtrate was concentrated. Purification by column chromatography (DCM/MeOH/aq. NH3 gradient) gave the title compound (122 mg, 94%) as a yellow solid.

Workup

customuntil bubbling
filtrationThe suspension was filtered
concentrationthe filtrate was concentrated
customPurification by column chromatography (DCM/MeOH/aq. NH3 gradient)

Sources & evidence

ORD record: ord-ee7f67dc7d204d728b748196278c441e
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786120B2

Reaction notes

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