Carbon tetrabromide → 3'-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile

HRID 478236Notes

Reaction equation

HRID 478236 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[N:4]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Na].[NH:51]1[CH:55]=[N:54][CH:53]=[N:52]1>ClCCl>[N:51]1([CH2:2][C:3]2[CH:8]=[CH:7][N:6]3[C:9]([C:12]4[CH:13]=[C:14]([C:18]5[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH:15]=[CH:16][CH:17]=4)=[CH:10][N:11]=[C:5]3[N:4]=2)[CH:55]=[N:54][CH:53]=[N:52]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 180012733'-(7-Hydroxymethylimidazo[1,2-a]pyrimidin-3-yl)-biphenyl-2-carbonitrileHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 101564263'-[7-([1,2,4]Triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrileYield 13.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3′-(7-hydroxymethylimidazo[1,2-a]pyrimidin-3-yl)-biphenyl-2-carbonitrile (0.1 g, 0.31 mmol) in dichloromethane (5 ml) was added carbon tetrabromide (153 mg, 0.46 mmol) and triphenylphosphine (121 mg, 0.46 mmol). This mixture was stirred at ambient temperature for 6 h after which time 1,2,4-triazole sodium salt (84 mg, 0.93 mmol) was added and the reaction stirred at ambient temperature for a further 18 h. The solvent was removed in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane on a gradient of methanol (0-10%). Further purification by high performance liquid chromatography gave 3′-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-a]pyrimidin-3-yl]biphenyl-2-carbonitrile (15.3 mg): δH (400 MHz, DMSO) 5.76 (2H, s), 7.32 (1H, d, J 7), 7.52-7.84 (8H, m), 8.16 (2H, d, J 5), 8.73 (1H, s), 9.22 (1H, s); m/z (ES+) 378 (M++H).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography
  4. washeluting with dichloromethane on a gradient of methanol (0-10%)
  5. customFurther purification by high performance liquid chromatography

Sources & evidence

ORD record
ord-5fa89201e1514e85b78c5c438c17d266
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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