Trityl chloride → 7-bromo-2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidine

HRID 920670Notes

Reaction equation

HRID 920670 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:8]2[N:9]=[C:10]([Cl:13])[N:11]=[CH:12][C:7]=2[NH:6][CH:5]=1.Cl[C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[Br:3][C:4]1[C:8]2[N:9]=[C:10]([Cl:13])[N:11]=[CH:12][C:7]=2[N:6]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 867311617-Bromo-2-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 867311637-bromo-2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidineYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of NaH (300 mg, 60% in mineral oil, 7.5 mmol) in THF (30 mL) was added a solution of 7-bromo-2-chloro-5H-pyrrolo[3,2-d]pyrimidine (1.16 g, 5.0 mmol) in THF (20 mL) dropwise at 0° C. After 20 min, a solution of TrCl (1.674 g, 6 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred for 6 hours, quenched with brine and extracted with EtOAc (3×). The combined organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by ISCO to provide the desired product (2.38 g, >99%). 1H NMR (400 MHz, CD3OD) δ 7.63 (s, 1H), 7.57 (s, 1H), 7.37-7.32 (m, 9H), 7.14-7.11 (m, 6H).

Workup

  1. customquenched with brine
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by ISCO

Sources & evidence

ORD record
ord-ffa37e89122a4380bab2baeeb457dbe2
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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