Ethanol → HCID 58180905, compound

HRID 1772824Notes

Reaction equation

HRID 1772824 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH:7]([N:11]2[CH:15]=[C:14]([C:16]3[C:17]4[CH:24]=[CH:23][NH:22][C:18]=4[N:19]=[CH:20][N:21]=3)[CH:13]=[N:12]2)[CH2:8][C:9]#[N:10])[CH2:3][CH2:2]1.[Cl:25][C:26]1[C:31]([CH3:32])=[C:30](Cl)[N:29]=[CH:28][N:27]=1.C(N(CC)C(C)C)(C)C.C(O)C>>[Cl:25][C:26]1[N:27]=[CH:28][N:29]=[C:30]([N:1]2[CH2:2][CH2:3][CH:4]([CH:7]([N:11]3[CH:15]=[C:14]([C:16]4[C:17]5[CH:24]=[CH:23][NH:22][C:18]=5[N:19]=[CH:20][N:21]=4)[CH:13]=[N:12]3)[CH2:8][C:9]#[N:10])[CH2:5][CH2:6]2)[C:31]=1[CH3:32]

Participants

5

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 8188604,6-Dichloro-5-methylpyrimidineHCID 58180923HCID 58180923, compound

Product 1

HCID 58180905HCID 58180905, compoundYield 44.3%

Procedure

A solution of 3-piperidin-4-yl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.20 g, 0.00062 mol), 4,6-dichloro-5-methylpyrimidine (0.11 g, 0.00067 mol) and N,N-diisopropylethylamine (130 microL, 0.00076 mol) in ethanol (2.0 mL, 0.034 mol) was heated to reflux for 1.2 hours, then the reaction was purified by preparative-LCMS (pH 10) to give 123 mg white solid (44% yield). LCMS (M+1): 448.

Workup

  1. temperatureto reflux for 1.2 hours
  2. customthe reaction was purified by preparative-LCMS (pH 10)

Sources & evidence

ORD record
ord-4aa702a8da06473cb9b8ee3ad062bc23
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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