4-Methylmorpholine → Prop-1-en-2-yl 6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-ylcarbamate

HRID 2069155노트

반응식

HRID 2069155 반응식
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CN1CCOCC1.[C:29](Cl)(=[O:34])[O:30][C:31]([CH3:33])=[CH2:32]>C1COCC1>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:29](=[O:34])[O:30][C:31]([CH3:33])=[CH2:32])[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 93846Isopropenyl chloroformateHCID 585325356-(4-Nitronaphthalen-1-yloxy)pyrimidin-4-amine

생성물 1

HCID 67422372Prop-1-en-2-yl 6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-ylcarbamate수율 94.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-amine (89 mg, 0.315 mmol) and NMM (45 μl, 0.410 mmol) in THF (2.0 mL) at 0° C. was added, dropwise, a solution of prop-1-en-2-yl carbonochloridate (45 μl, 0.410 mmol) in THF (1.0 mL) and the reaction mixture warmed to RT for 15 hr and then partitioned between EtOAc (20 mL) and water (5.0 mL). The aq layer was separated and extracted with EtOAc and the combined organic layers were dried (MgSO4) and then evaporated in vacuo to afford the title compound as a yellow oil (109 mg, 87%); Rt 2.54 min (Method 2); m/z 367 (M+H)+ (ES+). This material was used directly in the next step (below) without further purification.

후처리

  1. custompartitioned between EtOAc (20 mL) and water (5.0 mL)
  2. customThe aq layer was separated
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-e3d80df895f443f1b1f196ef415df06c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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