Hydrochloric Acid → N-Butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amine

HRID 920662

Reaction equation

HRID 920662 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:11]([NH2:15])[CH2:12][CH2:13][CH3:14].Cl>CC(O)C>[CH2:11]([NH:15][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 86731154N-Butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amineYield 96%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A suspension of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (0.62 g, 4 mmol) in 5 mL iPrOH was added nBuNH2 (2.5 mL, 25.3 mmol) and followed by HCl (2.0 mL, 4.0 M in dioxanes, 8 mmol). The resulting solution was heated at 170° C. for 1 h under microwave irradiation. The reaction was monitored by LC-MS. The reaction time should be extended whenever it is necessary. After evaporation of solvents, the crude product was washed with minimal amount of MeOH. The solid was collected. And the MeOH filtrate was purified by ISCO to provide the desired product (0.73 g, 96%). 1H NMR (400 MHz, CD3OD) δ 8.42 (d, J=0.8 Hz, 1H), 7.53 (d, J=3.1 Hz, 1H), 6.27 (dd, J=3.0, 0.8 Hz, 1H), 3.37 (t, J=7.1 Hz, 2H), 1.68-1.57 (m, 2H), 1.52-1.36 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); MS m/z 191.2 [M+H]+.

Workup

  1. customAfter evaporation of solvents
  2. washthe crude product was washed with minimal amount of MeOH
  3. customThe solid was collected
  4. customAnd the MeOH filtrate was purified by ISCO

Sources & evidence

ORD record
ord-2c45cc994563467b8e682c133669308f
Source dataset
uspto-grants-2016_03
Patent number
US09273056B2

Linked notes

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