Triethylamine → 7-(4-((tert-Butyldimethylsilyl)oxy)cyclohex-1-en-1-yl)-2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidine

HRID 920672Notes

Reaction equation

HRID 920672 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:16]2[C:20]3[N:21]=[C:22]([Cl:25])[N:23]=[CH:24][C:19]=3[N:18]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:17]=2)(O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CS(Cl)(=O)=O.CCN(CC)CC>C(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:16]2[C:20]3[N:21]=[C:22]([Cl:25])[N:23]=[CH:24][C:19]=3[N:18]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:17]=2)=[CH:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867311624-((tert-Butyldimethylsilyl)oxy)-1-(2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohexanol

Product 1

HCID 867311647-(4-((tert-Butyldimethylsilyl)oxy)cyclohex-1-en-1-yl)-2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidineYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-((tert-butyldimethylsilyl)oxy)-1-(2-chloro-5-trityl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)cyclohex-anol (1.00 g, 1.6 mmol) in CH2Cl2 (20 mL) was added MsCl (275 mg, 2.4 mmol) followed by NEt3 (808 mg, 8 mmol). The reaction mixture was stirred at room temperature 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 (485 mg, 50%). 1H NMR (400 MHz, CDCl3) δ 7.56 (s, 1H), 7.34 (s, 1H), 7.25-7.21 (m, 9H), 7.08-7.05 (m, 6H), 6.89 (s, 1H), 3.90-3.86 (m, 1H), 2.49-2.43 (m, 1H), 2.37-2.28 (m, 1H), 2.19-2.13 (m, 1H), 1.85-1.82 (m, 1H), 1.68-1.62 (m, 2H), 0.82 (s, 9H), 0.00 (s, 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-8558d8495e1448929e167f62acde2b7f
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Reaction notes

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