Triethylamine → HCID 178425599, compound

HRID 2203300Notes

Reaction equation

HRID 2203300 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)=[C:4]([CH3:23])[CH:3]=1.C(N(CC)CC)C.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1>C(Cl)Cl>[CH3:23][C:4]1[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([CH3:40])[CH:32]=2)=[O:39])[CH:7]=[CH:6][C:5]=1[CH:8]1[CH2:22][N:12]2[C:13](=[O:21])[NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69303m-Tolyl isocyanate2×HCID 178428488HCID 178428488, compound

Product 1

HCID 178425599HCID 178425599, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(4-amino-2-methylphenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one (92 mg, 0.30 mmol) and triethylamine (0.125 mL, 0.90 mmol) in 2.5 mL CH2Cl2 at rt was added meta-tolyl isocyanate (0.057 mL, 0.45 mmol) and the reaction stirred at rt. After 2 hours, an additional 0.015 mL meta-tolyl isocyanate and 1.5 mL CH2Cl2 was added and the reaction continued for 20 hours. The reaction was quenched with 0.5 mL MeOH, stirred 5 minutes and then evaporated. The mixture was triturated with MeOH, filtered and rinsed with MeOH and EtOAc to give the title compound as an off-white solid (99 mg, 75%). 1H NMR (DMSO-d6) δ: 10.68 (s, 1H), 8.54 (d, J=3.2 Hz, 2H), 7.99 (dd, J=7.9, 1.5 Hz, 1H), 7.40-7.47 (m, 1H), 7.00-7.32 (m, 8H), 6.78 (d, J=7.0 Hz, 1H), 4.15-4.23 (m, 1H), 3.63-3.73 (m, 1H), 3.44-3.55 (m, 2H), 3.04-3.16 (m, 1H), 2.31 (s, 3H), 2.27 (s, 3H).

Workup

  1. waitthe reaction continued for 20 hours
  2. customThe reaction was quenched with 0.5 mL MeOH
  3. stirringstirred 5 minutes
  4. customevaporated
  5. customThe mixture was triturated with MeOH
  6. filtrationfiltered
  7. washrinsed with MeOH and EtOAc

Sources & evidence

ORD record
ord-0ee00dcf18c64c16a9f1c4892d82ddce
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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