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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 881569
Notes
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Reaction equation

HRID 881569 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 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

Reagents, catalysts & solvents

2
HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-6f722b48dad84a3c870768ce28aaf007
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes