HCID 67540580, compound → tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 1192300Notes

Reaction equation

HRID 1192300 reaction equation
C(O[K])(C)(C)C.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:25]([NH2:26])=[C:24]([C:27]#[C:28][Si](C)(C)C)[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CN1C(=O)CCC1>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:25]3[NH:26][CH:28]=[CH:27][C:24]=3[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 67540580HCID 67540580, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 67539894tert-Butyl 4-(5H-pyrrolo[3,2-d]pyrimidin-4-yl)piperazine-1-carboxylateYield 53%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of tBuOK (0.063 g, 0.56 mmol) in NMP (4 mL) was added 4-(5-Amino-6-trimethylsilanylethynyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.1 g, 0.27 mmol) in NMP (1 mL) under N2. The mixture was vigorously stirred at room temperature for 4 hours. The reaction was quenched with water (1 mL) and ethyl acetate (50 mL). The organic phase was washed brine and water until NMP was gone, then dried over MgSO4, filtered and concentrated. The residue was subject to chromatography on silica gel to afford the product 4-(5H-Pyrrolo[3,2-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (43 mg, 53%). 1H NMR (CDCl3, 400 Hz) δ 9.47 (s, 1H), 8.49 (s, 1H), 7.37 (d, J=2.4 Hz, 1H), 6.62 (d, J=2.8 Hz, 1H), 3.85-3.82 (m, 4H), 3.61-3.58 (m, 4H). 1.49 (s, 9H). MS (ESI+) [M+H]+ 304.

Workup

  1. customThe reaction was quenched with water (1 mL) and ethyl acetate (50 mL)
  2. washThe organic phase was washed brine and water until NMP
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0cb683e6150489f9ea853653a5824bb
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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