N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amine → N-(3-bromophenyl)-6-methoxypyrido[3,2-d]pyrimidin-4-amine

HRID 50772Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]1[C:7]2[N:15]=[C:14](F)[CH:13]=[CH:12][C:8]=2[N:9]=[CH:10][N:11]=1.[CH3:20][O-:21].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:6]2[C:7]3[N:15]=[C:14]([O:21][CH3:20])[CH:13]=[CH:12][C:8]=3[N:9]=[CH:10][N:11]=2)[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(3-Bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (described in a previous experimental) (0.11 g, 0.34 mmol) is added to a solution of NaOMe (prepared by the addition of Na metal (31 mg, 1.38 mmol) to dry MeOH (15 mL). After heating in a pressure vessel at 90° C. for 3 h, the solution is concentrated to dryness and the residue is partitioned between EtOAc and water. Workup of the organic portion gives 4-(3-bromophenyl) amino-6-methoxypyrido[3,2-d]pyrimidine (92 mg, 82%). 1H NMR (CDCl3) δ 8.73 (1H, s), 8.66 (1H, brs), 8.18 (1H, m), 8.05 (1H, d, J=8.9 Hz), 7.83-7.80 (1H, m), 7.30-7.24 (2H, m), 7.23 (1H, d, J=8.9 Hz), 4.12 (3H, s)

Workup

concentrationthe solution is concentrated to dryness
customthe residue is partitioned between EtOAc and water

Sources & evidence

ORD record: ord-8fb45fba38a24583b94d7075a7ffbb47
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713484B2

Reaction notes

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