Methanol → HCID 178487819, compound

HRID 2273241Notes

Reaction equation

HRID 2273241 reaction equation
CSC.B.[NH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH:12]2[O:25][C:24]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH3:27])[N:22]=4)[N:17]=[CH:16][C:15]=3[NH:14][C:13]2=O)[CH2:8][CH2:7]1.ClCCl.CO>O1CCCC1>[CH3:27][O:26][C:21]1[N:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]1[NH:14][CH2:13][CH:12]([C@H:9]3[CH2:10][CH2:11][C@H:6]([NH2:5])[CH2:7][CH2:8]3)[O:25][C:24]2=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 178487821HCID 178487821, compound

Product 1

HCID 178487819HCID 178487819, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane dimethyl sulfide complex (2M solution in tetrahydrofuran, 12.5 mL, 25.0 mmol, 10.0 eq) is added at room temperature to a stirred solution of 3-(trans-4-amino-cyclohexyl)-6-methoxy-1H-4-oxa-1,5,9-triaza-phenanthren-2-one (821 mg, 2.50 mmol, 1.0 eq) in tetrahydrofuran (80 mL). The reaction mixture is heated to reflux for 3 hours, cooled down to 0° C. and cautiously quenched with methanol (10 mL) and then evaporated to give a residue that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 1:1, v/v) to afford trans-4-(6-methoxy-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexylamine as a yellow solid (340 mg, 45% yield).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. customcautiously quenched with methanol (10 mL)
  4. customevaporated
  5. customto give a residue that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-204db53a25ff48ca8deffc2efff28fd2
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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