StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Trimethyl orthoformate → (S)-3-methyl-4-(6-((4-methylpiperazin-1-yl)methyl)-2-(pyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl)morpholine

HRID 391150
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 391150
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@@H:14]2[CH3:19])[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.[BH-](O[C:30]([CH3:32])=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.COC(OC)OC>ClCCCl.CC(O)=O>[CH3:19][C@H:14]1[CH2:15][O:16][CH2:17][CH2:18][N:13]1[C:4]1[C:5]2[S:10][C:9]([CH2:11][N:38]3[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]3)=[CH:8][C:6]=2[N:7]=[C:2]([C:30]2[CH:32]=[N:7][CH:2]=[N:3][CH:4]=2)[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 58234096(S)-2-chloro-4-(3-methylmorpholino)thieno[3,2-d]pyrimidine-6-carbaldehyde

Produkt 1

HCID 24948169(S)-3-methyl-4-(6-((4-methylpiperazin-1-yl)methyl)-2-(pyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Following General Procedure D, (S)-2-chloro-4-(3-methylmorpholino)thieno[3,2-d]pyrimidine-6-carbaldehyde (100 mg, 0.34 mmol), HOAc (25 mg), NaBH(OAc)3 (80 mg, 0.37 mmol), N-methylpiperazine (41 mg, 0.40 mmol), 1,2-dichloroethane (1.0 mL), trimethylorthoformate were reacted at room temperature. The crude product was used in the next step without purification. MS (Q1) 382 (M)+. Following General Procedure A, crude product from above, pyrimidine-5-boronic acid (27 mg), Pd(PPh3)4 (20 mg), MeCN (1 mL) and 1M KOAc in H2O (1 mL) were irradiated at 150° C. for 30 min. The reaction mixture was diluted with CH2Cl2, and filtered. The filtrate was concentrated to give crude 422 which was purified by reverse phase HPLC. (14 mg) MS (Q1) 426 (M)+

Aufarbeitung

  1. customwere reacted at room temperature
  2. customThe crude product was used in the next step without purification
  3. customwere irradiated at 150° C. for 30 min
  4. additionThe reaction mixture was diluted with CH2Cl2
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto give crude 422 which
  8. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7b21bba2047c4c99bb455428ff1a867f
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08383620B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion