Hydrogen Bromide → 4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-bromo-pyrido[2,3-d]pyrimidine

HRID 1434515

Reaction equation

[N:1]1([C:7]2[C:8]3[CH:25]=[C:24](N)[CH:23]=[N:22][C:9]=3[N:10]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].[BrH:37]>O>[N:1]1([C:7]2[C:8]3[CH:25]=[C:24]([Br:37])[CH:23]=[N:22][C:9]=3[N:10]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-amino-pyrido[2,3-d]pyrimidine (1.45 g; 4 mmol) and cuprous bromide (1.15 g; 8 mmol) was dissolved in a mixture of water (25 mL) and concentrated hydrobromic acid (25 mL). The solution was chilled in an ice bath, and to it was added sodium nitrite (340 mg; 5 mmol, in aqueous solution). The solution was stirred for ten minutes, and then heated to 60° C. for one hour. It was then poured into a 10% solution of potassium carbonate, and extracted with dichloromethane (2×50 mL). The organic layer was dried over magnesium sulfate, evaporated, and the product was purified by column chromatography to give 4-morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-bromo-pyrido[2,3-d]pyrimidine (0.98 g).

Workup

temperatureThe solution was chilled in an ice bath
extractionextracted with dichloromethane (2×50 mL)
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated
customthe product was purified by column chromatography

Sources & evidence

ORD record: ord-e2907b27552c45cda528ad756574b70f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615552B2

Linked notes

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