Hydrochloric Acid → 5-Bromo-2-{4-[3-(isobutylamino)-2-hydroxypropoxy]anilino}-4-(4-methoxyphenoxy)pyrimidine

HRID 49798Notes

Reaction equation

Cl.[Br:2][C:3]1[C:4]([O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]([OH:23])[CH2:19][N:20]([CH3:22])C)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[CH2:33](NCC(O)COC1C=CC(N)=CC=1)[CH:34](C)[CH3:35]>CN1C(=O)CCC1>[Br:2][C:3]1[C:4]([O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[N:5][C:6]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH:18]([OH:23])[CH2:19][NH:20][CH2:22][CH:34]([CH3:35])[CH3:33])=[CH:14][CH:15]=2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethereal hydrogen chloride (2.0M; 0.57 ml, 1.14 mmol) was added to a solution of 5-bromo-2-chloro-4-(4-methoxyphenoxy)pyrimidine (Method 1, 200 mg, 0.63 mmol) and 4-[3-(isobutylamino)-2-hydroxypropoxy]aniline (Method 10, 136 mg, 0.57 mmol) in NMP (4 ml). The solution was heated at 100° C. for 6 hours and silica (1 g) was added. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluting with 0-10% 2.0M methanolic ammonia solution in DCM, to give the product as a colourless solid (76 mg, 26%). MS (MH+): 517, 519; HPLC (RT): 6.48.

Workup

additionsilica (1 g) was added
customVolatile material was removed by evaporation
customthe residue was purified by column chromatography
washeluting with 0-10% 2.0M methanolic ammonia solution in DCM

Sources & evidence

ORD record: ord-4212b4b90fd34d8c9d6c6dceb426ff5f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710052B2

Reaction notes

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