N-bromobutanimide → 5H-Pyrrolo3,2-dpyrimidin-2-amine, 7-bromo-4-(phenylmethoxy)-5-(phenylmethoxy)methyl-

HRID 1349348Notes

Reaction equation

HRID 1349348 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]2[N:10]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Br:28]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:5]2[N:10]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[C:8]([Br:28])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 222224585H-Pyrrolo3,2-dpyrimidin-2-amine, 4-(phenylmethoxy)-5-(phenylmethoxy)methyl-

Product 1

HCID 118122125H-Pyrrolo3,2-dpyrimidin-2-amine, 7-bromo-4-(phenylmethoxy)-5-(phenylmethoxy)methyl-Yield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-amino-4-benzyloxy-5-N-benzyloxymethylpyrrolo[3,2-d]pyrimidine (1.0 g) in methylene chloride (30 mL) was stirred in an ice bath while N-bromosuccinimide (0.5 g) was added portion-wise. The solution was concentrated and chromatography afforded 2-amino-4-benzyloxy-5-N-benzyloxymethyl-7-bromopyrrolo[3,2-d]pyrimidine (1.15 g) as a white solid. 13C NMR (CDCl3) δ 158.8, 157.2, 150.9, 137.3, 136.6, 131.8, 129.0, 128.8, 128.6, 128.5, 128.3, 127.9, 111.3, 90.3, 77.8, 70.7, 68.4.

Workup

  1. additionwas added portion-wise
  2. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-cb3dc5fcddce4e518807766156019916
Source dataset
uspto-grants-2007_05
Patent number
US07211677B2

Reaction notes

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