HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N-(tert-Butyl)-7-chlorothiazolo[5,4-d]pyrimidin-2-amine → HCID 58095024, compound

HRID 2282329
Notes
Print preview

Reaction equation

HRID 2282329 reaction equation
[C:1]([NH:5][C:6]1[S:7][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:13]=2[N:14]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:24]1[S:25][C:26]([Sn](CCCC)(CCCC)CCCC)=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[Cl:36])[CH:17]=[CH2:18]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH2:16]([N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:24]1[S:25][C:26]([C:12]2[C:13]3[N:14]=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[S:7][C:8]=3[N:9]=[CH:10][N:11]=2)=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[Cl:36])[CH:17]=[CH2:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11572293N-(tert-Butyl)-7-chlorothiazolo[5,4-d]pyrimidin-2-amineHCID 58095051HCID 58095051, compound

Product 1

HCID 58095024HCID 58095024, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-Butyl-(7-chlorothiazolo[5,4-d]pyrimidin-2-yl)-amine (1.00 g, 4.12 mmol), 1-allyl-2-[3-(2,4-dichlorophenyl)-5-(tributylstannyl)-2-thienyl]-1H-imidazole (1.71 g, 2.75 mmol) and DMF (23 mL) was stirred and degassed with vacuum. The atmosphere was replaced with nitrogen and then bis(triphenylphosphine)palladium(II) chloride (96.4 mg, 0.137 mmol) was added to the mixture. The orange solution was heated at 100° C. for 3 hours and the mixture was allowed to cool to rt. Column chromatography was performed to yield the title compound (1.12 g, 75%) as a pale yellow solid. LCMS: (FA) ES+ 541, 543. 1H NMR (400 MHz, d6-DMSO) δ; 8.73 (bs, 1H), 8.65 (bs, 1H), 8.56 (bs, 1H), 7.75 (d, J=2.5 Hz, 1H), 7.38 (dd, J=8.5, 2.5 Hz, 1H), 7.21 (d, J=1.3 Hz, 1H), 7.12 (d, J=8.5 Hz, 1H), 7.05 (d, J=1.3 Hz, 1H), 5.64-5.55 (m, 1H), 5.06-5.03 (m, 1H), 4.84-4.79 (m, 1H), 4.31-4.27 (m, 2H), 1.49 (s, 9H).

Workup

  1. customdegassed with vacuum
  2. temperatureto cool to rt

Sources & evidence

ORD record
ord-e06b7c6e05514d5cb1f56579d954e770
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139589B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes