5-Bromo-2-chloro-4-(indan-5-ylamino)pyrimidine → 5-Bromo-2-{4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]anilino}-4-(indan-5-ylamino)pyrimidine

HRID 1357519Notes

Reaction equation

Cl.[OH:2][CH:3]([CH2:13][N:14]([CH3:16])[CH3:15])[CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.[Br:17][C:18]1[C:19]([NH:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH2:30][CH2:29]3)=[N:20][C:21](Cl)=[N:22][CH:23]=1>CO.C(O)CCC>[Br:17][C:18]1[C:19]([NH:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH2:30][CH2:29]3)=[N:20][C:21]([NH:10][C:9]2[CH:11]=[CH:12][C:6]([O:5][CH2:4][CH:3]([OH:2])[CH2:13][N:14]([CH3:16])[CH3:15])=[CH:7][CH:8]=2)=[N:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A hot solution of 4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride (Method 89, 156 mg, 0.56 mmol) in methanol (2 ml) was added to a solution of 5-bromo-2-chloro-4-(indan-5-ylamino)pyrimidine (Method 15, 200 mg, 0.62 mmol) in n-butanol (20 ml). The mixture was heated at 100° C. for 18 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 (117 mg, 42%). NMR: 2.03 (m, 2H), 2.18 (s, 6H), 2.32 (m, 2H), 2.83 (m, 4H), 3.80 (m, 3H), 4.76 (d, 1H), 6.70 (d, 2H), 7.17 (m, 1H), 7.23 (m, 1H), 7.41 (m, 3H), 8.10 (s, 1H), 8.35 (s, 1H), 9.03 (s, 1H); MS (MH+): 498.4, 500.4.

Workup

addition(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-cbe3565d4b7047989db08c2c7b3acb00
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06593326B1

Reaction notes

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