Dichloromethane → 9-(Cyclohexylmethyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 2428023Notes

Reaction equation

HRID 2428023 reaction equation
[NH2:1]/[C:2](/[C:17]#[N:18])=[C:3](\[NH:6][C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])/[C:4]#[N:5].N/[C:20](=[C:23](\N)/C#N)/[C:21]#N.N(CC1CCCCC1)=C=[O:29].ClCCl.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH:11]1([CH2:10][N:9]2[C:7](=[O:8])[NH:6][C:3]3[C:4]2=[N:5][C:41]([C:42]2[CH:23]=[CH:20][CH:21]=[C:44]([OH:40])[CH:43]=2)=[N:1][C:2]=3[C:17]([NH2:18])=[O:29])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 2723951DiaminomaleonitrileHCID 3414518(Isocyanatomethyl)cyclohexaneHCID 57474758(Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea

Product 1

HCID 574747579-(Cyclohexylmethyl)-2-(3-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamideYield 47%

Procedure

(Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea. 2,3-Diaminomaleonitrile (0.119 g, 1.10 mmol) and (isocyanatomethyl)cyclohexane (0.140 g, 1.00 mmol) in tetrahydrofuran (2 mL) were reacted according to General Procedure A. Dichloromethane and hexanes were added to the solution and the resultant precipitate was filtered and dried to afford the title compound (0.200 g, 47%). MS (ESI) m/z 248.2 [M+1]+.

Workup

  1. filtrationthe resultant precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-6a2ab5ada52149119e7bb5737574d117
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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