Morpholine → HCID 135581741, compound

HRID 333706Notes

Reaction equation

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

Participants

Reactant 2

HCID 8083Morpholine

HCID 59026631HCID 59026631, compound

Product 1

HCID 135581741HCID 135581741, compound

Conditions

Temperature: 200 °C

Procedure

A mixture of N-(2-cyano-5-(4-fluorophenyl)thiophen-3-yl)-2-methoxybenzamide (0.10 g, 0.57 mmol) and morpholine (0.20 mL) was heated in a microwave oven at 200° C. for 5 min. The reaction was purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 2-(6-(4-fluorophenyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)phenol. LC/MS: m/z 408 (M+H)+ at 4.76 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

customThe reaction was purified by preparative reverse phase

Sources & evidence

ORD record: ord-a82f128c05e24702b7d504885dfa1a25
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883781B2

Reaction notes

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