Allyl bromide → HCID 13321945, compound

HRID 1284892Notes

Reaction equation

HRID 1284892 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([NH2:19])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].N1(C2CCCCCCCCCC2)CCCCCC[CH2:24][CH2:23][CH2:22]N1.[CH2:42](Br)[CH:43]=[CH2:44]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([N:19]([CH2:44][CH:43]=[CH2:42])[CH2:24][CH:23]=[CH2:22])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 13321944HCID 13321944, compoundHCID 57346892Diazabicycloundecane

Product 1

HCID 13321945HCID 13321945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 0.4 g of 8-amino-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 11) is agitated in 8 ml of ethanol with 0.16 ml of diazabicycloundecane and 0.25 ml of allyl bromide for 5 hours at 50°-60° C. The reaction solution is subsequently evaporated, and the residue is taken up in ethyl acetate. This solution is washed first with water, then with sodium bicarbonate solution, and finally again with water, dried with sodium sulfate, and concentrated, thus obtaining 0.18 g of 8-diallylamino-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 188°-190° C.

Workup

  1. customThe reaction solution is subsequently evaporated
  2. washThis solution is washed first with water
  3. dry with materialwith sodium bicarbonate solution, and finally again with water, dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60413556497d47c5b3c0e324d2b6d36d
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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