Diisopropylethylamine → Aim-100

HRID 502652Notes

Reaction equation

HRID 502652 reaction equation
Br[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1NC.C[CH2:31][N:32](C(C)C)C(C)C>C(O)CCC>[C:11]1([C:10]2[C:3]3[C:2]([NH:32][CH2:31][C@@H:24]4[CH2:25][CH2:26][CH2:27][O:23]4)=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 586033114-Bromo-5,6-diphenyl-furo[2,3-d]pyrimidineHCID 66683780(S)-(tetrahydrofuran-2-yl)-methylamine

Product 1

HCID 11501591Aim-100Yield 95%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

Compound 69 (60 mg, 0.17 mmol), (S)-tetrahydrofuran-2-yl-methylamine (36 μL, 0.34 mmol), and DIEA 150 μL (0.86 mmol) were mixed in 1-butanol (2 mL) and heated to 120° C. for 1.5 h. The reaction mixture was concentrated, and the residue was purified by flash chromatography to yield a white solid (60 mg). MS: 372.1 (M+1). 1HNMR (DMSO-d6) ppm 8.36 (s, 1H), 7.61-7.34 (m, 10H), 5.11 (t, 1H), 3.89-3.85 (m, 1H), 3.58-3.48 (m, 4H), 1.84-1.64 (m, 3H), 1.40-1.38 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b4a3fc13682049a797ecb96830a70510
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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