1,4,5,6-Tetrahydropyrimidin-2-amine → HCID 86594980, compound

HRID 1759710Notes

Reaction equation

HRID 1759710 reaction equation
[NH2:1][C:2]1[NH:3][CH2:4][CH2:5][CH2:6][N:7]=1.[Br:8][C:9]1[CH:42]=[CH:41][C:12]2[N:13]=[C:14]([NH:16][C@H:17]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:21][CH:20]=3)[S:15][C:11]=2[CH:10]=1.NN1C=CCNC1>C1COCC1>[Br:8][C:9]1[CH:42]=[CH:41][C:12]2[N:13]=[C:14]([NH:16][C@H:17]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29](=[O:30])[NH:1][C:2]4[NH:7][CH2:6][CH2:5][CH2:4][N:3]=4)=[CH:23][CH:24]=3)[S:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 32874121,4,5,6-Tetrahydropyrimidin-2-amineHCID 18176952HCID 18176952, compoundHCID 86594978HCID 86594978, compound

Product 1

HCID 86594980HCID 86594980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg of 2-amino-1,4,5,6-tetrahydropyrimidine is added to a solution of the ester 8-2 (123 mg) in 3 ml of THF, agitation is carried out for 20 hours at ambient temperature, 48 mg of tetrahydroaminopyrimidine is also added and agitation is carried out for 5 hours. After evaporating under reduced pressure, the mixture is chromatographed eluting with a CH2Cl2/AcOEt 80/20 then CH2Cl2/MeOH 90/10 mixture. 68 mg of the expected 8-3 is obtained.

Workup

  1. waitagitation is carried out for 5 hours
  2. customAfter evaporating under reduced pressure
  3. customthe mixture is chromatographed
  4. washeluting with a CH2Cl2/AcOEt 80/20
  5. customis obtained

Sources & evidence

ORD record
ord-09eea61a02544d91825633276b7fb859
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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