N-bromobutanimide → HCID 67960573, compound

HRID 2362328Notes

Reaction equation

HRID 2362328 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:15](=[O:17])[N:14]([CH2:18][C:19]4[N:28]=[C:27]([CH3:29])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)[C:13]4=[N:30][CH2:31][CH2:32][N:12]4[C:11]=3[N:10]=[CH:9]2)=CC=1.C1C(=O)N([Br:42])C(=O)C1>CC#N>[Br:42][C:9]1[NH:8][C:16]2[C:15](=[O:17])[N:14]([CH2:18][C:19]3[N:28]=[C:27]([CH3:29])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[C:13]3=[N:30][CH2:31][CH2:32][N:12]3[C:11]=2[N:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 67960315HCID 67960315, compound

Product 1

HCID 67960573HCID 67960573, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 5-((4-methylquinazolin-2-yl)methyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one 13 (386 mg, 1.16 mmol) in CH3CN (10 ml) was added NBS (268 mg, 1.51 mmol) at 0° C., stirred for 1.5 hr. Another 41 mg of NBS was added, stirred for 30 minutes. The reaction was quenched by adding water (15 ml), washed with DCM (2×15 ml). The organic phase was washed with HCl (1 M, 10 ml). The combined aqueous phase was concentrated and purified by flash chromatography (MeOHIDCM, MeOH contains 1% Et3N) to afford 2-bromo-5-((4-methylquinazolin-2-yl)methyl)-7,8-dihydro-3H-imidazo[2,1-b]purin-4(5H)-one 14.

Workup

  1. stirringstirred for 30 minutes
  2. customThe reaction was quenched
  3. additionby adding water (15 ml)
  4. washwashed with DCM (2×15 ml)
  5. washThe organic phase was washed with HCl (1 M, 10 ml)
  6. concentrationThe combined aqueous phase was concentrated
  7. custompurified by flash chromatography (MeOHIDCM, MeOH contains 1% Et3N)

Sources & evidence

ORD record
ord-160b236dd91d4e95b5db5af6ef0f5538
Source dataset
uspto-grants-2014_04
Patent number
US08691832B2

Reaction notes

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