(Dimethyl sulfide)trihydroboron → HCID 178487820, compound

HRID 2273247Notes

Reaction equation

HRID 2273247 reaction equation
[CH3:1]SC.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>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[N:14]([CH3:1])[CH2:13][CH:12]([C@H:9]3[CH2:8][CH2:7][C@H:6]([NH2:5])[CH2:11][CH2:10]3)[O:25][C:24]2=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 178487821HCID 178487821, compound

Product 1

HCID 178487820HCID 178487820, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Borane dimethyl sulfide complex (2M solution in tetrahydrofuran, 60.0 mL, 120.0 mmol, 24.5 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 (1.67 g, 4.88 mmol, 1.0 eq) in tetrahydrofuran (600 mL). The reaction mixture is heated to reflux for 3 hours, cooled down to 0° C. and cautiously quenched with methanol (100 mL) and then evaporated to give crude trans-4-(6-methoxy-1-methyl-2,3-dihydro-1H-4-oxa-1,5,9-triaza-phenanthren-3-yl)-cyclohexylamine that is directly engaged in the next step.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. customcautiously quenched with methanol (100 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-73639f00aad040aca1e378c080dc73d1
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

Loading…