Phenyl isocyanate → HCID 178521958, compound

HRID 2203274Notes

Reaction equation

HRID 2203274 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:22][N:12]3[C:13](=[O:21])[NH:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10][CH2:9]2)=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[O:21]=[C:13]1[N:12]2[CH2:22][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:30]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:31])=[CH:3][CH:4]=3)[CH2:9][N:10]=[C:11]2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:14]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 178507413HCID 178507413, compound

Product 1

HCID 178521958HCID 178521958, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-aminophenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (25.1 mg, 0.086 mmol) in 1.1 mL THF was added phenyl isocyanate (0.0103 mL, 0.095 mmol) and the reaction stirred at rt. After 45 min, the reaction was briefly warmed to approximately 50° C. and then allowed to cool to rt. At 2.5 hours the reaction was quenched with MeOH, evaporated, then triturated with MeOH, EtOAc, and then 50% EtOAc/hexane to give the title compound as a light tan solid (25.0 mg, 71%). 1H NMR (DMSO-d6) δ: 10.69 (br. s, 1H), 8.64 (br. s, 2H), 7.98 (d, J=7.0 Hz, 1H), 7.40-7.47 (m, 5H), 7.21-7.31 (m, 4H), 6.92-7.10 (m, 3H), 4.18-4.26 (m, 1H), 3.67-3.77 (m, 1H), 3.49-3.61 (m, 2H), 2.89-3.03 (m, 1H).

Workup

  1. temperaturethe reaction was briefly warmed to approximately 50° C.
  2. temperatureto cool to rt
  3. customAt 2.5 hours the reaction was quenched with MeOH
  4. customevaporated
  5. customtriturated with MeOH, EtOAc

Sources & evidence

ORD record
ord-997986b5309c4143980cf3e76353fa0b
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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