Sodium Carbonate → 4-(2,4-di-tert-butoxypyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1042260Notes

Reaction equation

HRID 1042260 reaction equation
[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9](B(O)O)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:27]1[C:28]2[CH:35]=[CH:34][NH:33][C:29]=2[N:30]=[CH:31][N:32]=1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([C:27]2[C:28]3[CH:35]=[CH:34][NH:33][C:29]=3[N:30]=[CH:31][N:32]=2)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2735950(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 687260714-(2,4-di-tert-butoxypyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 72%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Di-tert-butoxypyrimidin-5-ylboronic acid (17.5 g, 65.4 mmol), tetrakis(triphenylphosphine) palladium(0) (7.6 g, 6.54 mmol) and sodium carbonate (20.8 g, 196 mmol) were added to a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 65.4 mmol) in DME (400 mL) and water (150 mL). With vigorous stirring, the mixture was heated to 80° C. for 24 h. The reaction mixture was cooled to RT and poured into water (100 mL). The mixture was extracted with EtOAc (100 mL) twice. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude product. This was purified by flash chromatography to give 4-(2,4-di-tert-butoxypyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (16.0 g, 72%) as a yellow solid. MS (APCI, pos. ion) m/z: 342.1 [M+H]+

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted with EtOAc (100 mL) twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-2a0aae788b74406e95e301771b969413
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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