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

HRID 2069155Notes

Reaction equation

HRID 2069155 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3d80df895f443f1b1f196ef415df06c
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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