Ammonia → 5-{4-[5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinamide

HRID 2102381Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[N:24][CH:25]=[C:26]([CH:31]=4)[C:27]([O:29]C)=O)=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[NH3:32]>C(O)CCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[N:24][CH:25]=[C:26]([CH:31]=4)[C:27]([NH2:32])=[O:29])=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

Methyl 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinate (0.015 g, 0.034 mmol) and ammonia (3.00 mL, 20%, 0.02 mol) were mixed in 1-butanol (1.00 mL) and the resulting mixture was heated at 180° C. for 20 h. The solvent was removed by evaporation, and the product was purified by preparative HPLC to give 5 mg (36%) 5-{4-[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]butoxy}nicotinamide hydroformate as a white solid. MS [M+H]=423.1, LC/MS (EI) tR 3.45 min (Method D), 1H NMR (7% MeOD/CDCl3) δ (ppm) 8.92 (s, 1H), 8.50 (s, 1H), 8.25 (s, 1H), 7.62 (s, 1H), 7.40-7.30 (m, 3H), 7.10 (t, J=8.4 Hz, 2H), 3.84 (t, J=6.0 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 1.75-1.58 (m, 2H), 1.59-1.45 (m, 2H).

Workup

customThe solvent was removed by evaporation
customthe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-169b8aff2fd148f3b81c719b71119cef
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576080B2

Reaction notes

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