Water → N2-(4-bromo-3-methoxyphenyl)-N4-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamine

HRID 2370111Notes

Reaction equation

HRID 2370111 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:17][CH3:18])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][C:21]=1[O:27][CH3:28].OS(O)(=O)=O.O>CN1C(=O)CCC1>[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[N:3]=[C:4]([NH:17][CH3:18])[C:5]3[CH2:10][CH2:9][CH:8]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:6]=3[N:7]=2)=[CH:22][C:21]=1[O:27][CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 70182544-Bromo-3-methoxyanilineHCID 580752952-chloro-N-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine

Product 1

HCID 50913346N2-(4-bromo-3-methoxyphenyl)-N4-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diamineYield 91.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloro-N-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (Preparation Ga) (0.24 g, 0.924 mmol), 4-bromo-3-methoxyaniline (0.187 g, 0.924 mmol) and H2SO4 (0.064 mL, 1.201 mmol) in NMP (Volume: 2 mL) was stirred in a sealed microwave tube at 90° C. overnight. The reaction was poured into 20 mL of water. The precipitate was collected by filtering. The cake was air dried. The cake was triturated with a minimum amount of cold MeOH to get 0.36 g (84%) of product as an off-white solid. LC-MS (M+H)+=425.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.39 (1 H, br. s.), 7.68 (1 H, d, J=1.51 Hz), 7.53 (1 H, d, J=8.53 Hz), 7.34-7.42 (2 H, m), 7.24-7.34 (3 H, m), 6.94 (1 H, dd, J=8.66, 2.38 Hz), 4.36-4.51 (1 H, m), 3.83 (3 H, s), 3.05 (3 H, d, J=4.52 Hz), 2.79-2.95 (1 H, m), 2.59-2.77 (2 H, m), 1.93-2.12 (1 H, m).

Workup

  1. customThe precipitate was collected
  2. filtrationby filtering
  3. customdried
  4. customThe cake was triturated with a minimum amount of cold MeOH

Sources & evidence

ORD record
ord-128377bedb2e4cf1a39137f8339d4305
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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