Diisopropylethylamine → HCID 68157965, compound

HRID 243495Notes

Reaction equation

HRID 243495 reaction equation
[Br:1][C:2]1[C:7]2[N:8]([CH3:14])[C:9]([C@@H:11]([NH2:13])[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[C:20](Cl)[N:19]=[CH:18][N:17]=1.CCN(C(C)C)C(C)C>CC(O)C>[NH2:15][C:16]1[C:21]([C:22]#[N:23])=[C:20]([NH:13][C@H:11]([C:9]2[N:8]([CH3:14])[C:7]3[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=3[N:10]=2)[CH3:12])[N:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122782624-Amino-6-chloropyrimidine-5-carbonitrileHCID 68157847HCID 68157847, compound

Product 1

HCID 68157965HCID 68157965, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (S)-1-(7-bromo-1-methyl-1H-benzoimidazol-2-yl)ethylamine (1 g, 3.9 mmol), 4-amino-6-chloropyrimidine-5-carbonitrile (0.64 g, 4.1 mmol) and DIPEA (2.1 mL, 4.1 mmol) in IPA (7.8 mL) was heated for 16 h at 90° C. After cooling to RT, the reaction mixture was filtered and the solid washed with MeOH and DCM to afford 421 as a cream solid (1.05 g, 72%). LCMS (Method K): RT 3.27 min [M+H]+ 372 (for 79Br) 1H NMR (DMSO-d6, 400 MHz): δ 8.07 (1H, s), 7.79 (1H, d, J=7.5 Hz), 7.63 (1H, d, J=8.0 Hz), 7.41 (1H, d, J=4.0 Hz), 7.32 (2H, bs), 7.11 (1H, dd, J=8.0, 8.0 Hz), 5.70 (1H, dq, J=7.5, 7.0 Hz), 4.01 (3H, s), 1.60 (3H, d, J=7.0 Hz)

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. washthe solid washed with MeOH and DCM

Sources & evidence

ORD record
ord-6ec29ef9273b4042a9626ec9390472dc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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