2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 69707591, compound

HRID 2184058Notes

Reaction equation

HRID 2184058 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[N:13][CH:12]=1.Br[C:18]1[N:22]2[CH:23]=[CH:24][C:25]([C:27]([OH:30])([CH3:29])[CH3:28])=[N:26][C:21]2=[N:20][CH:19]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[N:26][C:21]3=[N:20][CH:19]=2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][N:14]=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 22329487HCID 22329487, compound

Product 1

HCID 69707591HCID 69707591, compound

Procedure

4-Fluoro-3-(pyridazin-4-yl)phenylboronic acid (100 mg, 0.46 mmol) was coupled to 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (117 mg, 0.46 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 5% methanol then trituration with diethyl ether gave 2-[3-(4-fluoro-3-(pyridazin-4-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol as a white solid: δH (400 MHz, CDCl3) 1.63 (6H, s), 7.11 (1H, d, J 7), 7.43-7.48 (1H, m), 7.64-7.69 (2H, m), 7.71-7.74 (1H, m), 7.88 (1H, s), 8.54 (1H, d, J 7), 9.33 (1H, dd, J 5 and 1), 9.46-9.47 (1H, m); m/z (ES+) 350 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 5% methanol

Sources & evidence

ORD record
ord-d5809a60e0a14c2f8773c628045de644
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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