Benzyl Bromide → HCID 70674575, compound

HRID 1747725Notes

Reaction equation

HRID 1747725 reaction equation
[CH:1]([OH:3])=[O:2].[NH2:4][C:5]1[C:10]([NH:11][C:12](=[O:15])[O:13][CH3:14])=[C:9]([NH2:16])[N:8]=[C:7]([C:17]2[N:18]=[C:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[N:21]3)[N:6]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[CH:1]([OH:3])=[O:2].[CH2:44]([N:11]([C:10]1[C:5]([NH2:4])=[N:6][C:7]([C:17]2[N:18]=[C:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[N:21]3)=[N:8][C:9]=1[NH2:16])[C:12](=[O:15])[O:13][CH3:14])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 70674229HCID 70674229, compound

Product 1

HCID 70674575HCID 70674575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

At 0° C., 100 mg (0.22 mmol) of methyl {4,6-diamino-2-[7-(2-fluorobenzyl)imidazo[1,5-b]pyridazin-5-yl]pyrimidin-5-yl}carbamate formate were initially charged in THF (0.94 ml), and 44.4 mg (0.24 mmol) of a 2 N solution of sodium bis(trimethylsilyl)amide in THF were added. After 30 min at 0° C., 52 μl (0.44 mmol) of benzyl bromide were added and the mixture was stirred at 20° C. for 20 hours. The reaction mixture was then concentrated and the residue was purified by preparative HPLC (acetonitrile/water (+0.1% formic acid) gradient). This gave 105 mg of the target compound (87% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by preparative HPLC (acetonitrile/water (+0.1% formic acid) gradient)

Sources & evidence

ORD record
ord-50c2c473a4af4a73b457a94e5eee605d
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

Loading…