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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 391150
ノート
印刷プレビュー

反応式

HRID 391150 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒
HCID 176Acetic Acid溶媒

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-7b21bba2047c4c99bb455428ff1a867f
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08383620B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート