Chloride → 6-Amino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-5-(2-(4-methoxybenzyloxy)-2-methyl-propionylamino)-2-thiouracil

HRID 2227360Notes

Reaction equation

HRID 2227360 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11])=[CH:5][CH:4]=1.[NH2:17][C:18]1[C:19](=[O:41])[NH:20][C:21](=[S:40])[N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=2)[C:23]=1[NH2:24].[Cl-]>C1COCC1>[NH2:24][C:23]1[N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=2)[C:21](=[S:40])[NH:20][C:19](=[O:41])[C:18]=1[NH:17][C:10](=[O:11])[C:9]([O:8][CH2:7][C:6]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 312ChlorideHCID 184734541-(3-Cyclopentyloxy-4-methoxy-benzyl)-5,6-diamino-2-thiouracilHCID 184736132-(4-Methoxybenzyloxy)-2-methyl-propionyl chloride

Product 1

HCID 184735306-Amino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-5-(2-(4-methoxybenzyloxy)-2-methyl-propionylamino)-2-thiouracil

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution with 2.91 g (12 mM) of crude 2-(4-methoxybenzyloxy)-2-methyl-propionyl chloride in 9 ml of THF was added within 90 min to a stirred suspension with 3.62 g (10 mM) of 5,6-diamino-1-(3-cyclopentyloxy-4-methoxy-benzyl)-2-thiouracil. After 20 hr another 485 mg of chloride in 5 ml of THF was added within 30 min. After a further 3 hr the solid was filtered off and the solution evaporated in vacuo to dryness. The residue was dissolved in ethyl acetate, extracted with sodium bicarbonate solution and the organic phase evaporated in vacuo to dryness. The residue was crystallized from methanol: 1.71 g (30.1%) of amide with mp 172-184° C.

Workup

  1. filtrationAfter a further 3 hr the solid was filtered off
  2. customthe solution evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted with sodium bicarbonate solution
  5. customthe organic phase evaporated in vacuo to dryness
  6. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-683fd301326b406490c46550db445777
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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