Methylamine → HCID 59242021, compound

HRID 1876188Notes

Reaction equation

HRID 1876188 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH3:9])[C:5]2[CH2:18][CH2:19][CH2:20][C:4]=2[N:3]=1.[CH2:21]([N:23](C(C)C)C(C)C)C.CN>C(O)(C)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([N:8]([CH3:9])[C:6]2[C:5]3[CH2:18][CH2:19][CH2:20][C:4]=3[N:3]=[C:2]([NH:23][CH3:21])[N:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 86640060HCID 86640060, compound

Product 1

HCID 59242021HCID 59242021, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
110 °C

Procedure

Crude (2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-yl)-(4-methoxyphenyl)-methylamine (100 mg, 0.32 mmol) was dissolved in isopropanol (10 mL) followed by the addition of ethyl-diisopropyl-amine (83 mg, 0.64 mmol) and alcoholic methylamine (excess, 800 μL). The mixture was stirred for 3 days at 110° C. The mixtures were evaporated and the residue was dissolved in CH2Cl2 and extracted with HCl (1 N). The organic layer was dried with MgSO4 and concentrated. The title compound was purified by preparative RPLC. 1H NMR (CDCl3) δ 7.18 (d, 2H), 6.95 (d, 2H), 3.85 (S, 3H), 3.50 (s, 3H), 3.03 (d, 3H), 2.79 (m, 2H), 1.80-1.70 (m, 4H); LC-MS (ESI+; 285 ([M+H]+)).

Workup

  1. customThe mixtures were evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. extractionextracted with HCl (1 N)
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationconcentrated
  6. customThe title compound was purified by preparative RPLC

Sources & evidence

ORD record
ord-89de4c3b89dc41b1887d499f024dd540
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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