tert-Butanol → HCID 46701917, compound

HRID 2090459Notes

Reaction equation

HRID 2090459 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[N:5]=[C:4]([NH2:25])[N:3]=1.[NH:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(N(CC)C(C)C)(C)C.C(O)(C)(C)C>CO>[N:26]1([C:2]2[CH:7]=[C:6]([N:8]3[CH:17]([CH3:18])[CH2:16][C:15]4[C:10](=[CH:11][C:12]([C:19]5[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=5)=[CH:13][CH:14]=4)[CH2:9]3)[N:5]=[C:4]([NH2:25])[N:3]=2)[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 68163Hexahydro-1,4-diazepineHCID 81531DiisopropylethylamineHCID 59402369HCID 59402369, compound

Product 1

HCID 46701917HCID 46701917, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-6-[3-methyl-7-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine (18 mg, 0.050 mmol), 1,4-diazepane (15.0 mg, 0.150 mmol, Aldrich, Cat. No. H16604)) and N,N-diisopropylethylamine (20.0 uL, 0.115 mmol) in tert-butyl alcohol (0.5 mL, 5 mmol) was heated at 120° C. overnight. After cooling, the mixture was diluted with methanol, and purified by RP-HPLC (pH=10) to afford the desired product. (M+H)+: m/z=419.2.

Workup

  1. temperatureAfter cooling
  2. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-5414dc315f0b4c17b43cb95e8e56809b
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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