Dimethylformamide → 4-Amino-2-(4-phthalimidobut-2-ynylthio)pyrimidine

HRID 542480Notes

Reaction equation

HRID 542480 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].Cl[CH2:10][C:11]#[C:12][CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].CN(C=O)C.N12CCCCC1C=NCCC2>CCOC(C)=O.O>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:10][C:11]#[C:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]3[C:15]2=[O:24])[N:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 2375372-(4-chlorobut-2-yn-1-yl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 178507915HCID 178507915, compound

Product 1

HCID 202087134-Amino-2-(4-phthalimidobut-2-ynylthio)pyrimidineYield 94.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of thiocytosine (0.5 g.), N-(4-chlorobut-2-ynyl)phthalimide (1.03 g.), DMF (5 ml.) and 1,5-diazabicyclo[5,4,0]undec-5-ene (0.67 g.) was stirred for 2 hours. The solution was treated with water (20 ml.) and EtOAc (10 ml.) and the insoluble solid collected to give 4-amino-2-(4-phthalimidobut-2-ynylthio)pyrimidine (1.2 g.) m.p. 197°-202° (decomp.).

Workup

  1. customthe insoluble solid collected

Sources & evidence

ORD record
ord-647ff6b73fba46299c6db92f0c4f14a2
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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