Triethylamine → HCID 21998635, compound

HRID 1976558Notes

Reaction equation

HRID 1976558 reaction equation
[CH2:1]([O:8][C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:37]=[CH:38][C:39]=1[O:40][CH3:41])[CH2:26][N:27]1[C:34]([NH2:35])=[C:33]([NH2:36])[C:31](=[O:32])[NH:30][C:28]1=[S:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[NH2:35][C:34]1[N:27]([CH2:26][C:25]2[CH:37]=[CH:38][C:39]([O:40][CH3:41])=[C:23]([O:22][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:24]=2)[C:28](=[S:29])[NH:30][C:31](=[O:32])[C:33]=1[NH:36][C:10](=[O:11])[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14120512HCID 14120512, compoundHCID 21998636HCID 21998636, compound

Product 1

HCID 21998635HCID 21998635, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-benzyloxy-2-methyl-propionyl chloride (30.70 g, 144 mmole) in THF (100 ml) was added at 0-5° C. over 15 minutes to a stirred suspension of 1-(3-benzyloxy-4-methoxy-benzyl)-5,6-diamino-2-thiouracil (40.58 g, 100 mmole) and triethylamine (31.4 ml, 225 mmole) in THF (400 ml). After 1 hour the solid was filtered off and the solution evaporated to dryness in vacuo. The residue was suspended in a mixture of diethyl ether (400 ml), water (100 ml) and saturated sodium bicarbonate solution (60 ml). After crystallization for 60 hours the solid was collected and washed with ether and water to give 6-amino-1-(3-benzyloxy-4-methoxy-benzyl)-5-(2-benzyloxy-2-methyl-propionylamino)-2-thiouracil (42.23 g, 75.3%). Crystallization from ethyl acetate gave mp 123-125/184-187° C.

Workup

  1. filtrationAfter 1 hour the solid was filtered off
  2. customthe solution evaporated to dryness in vacuo
  3. additionThe residue was suspended in a mixture of diethyl ether (400 ml), water (100 ml) and saturated sodium bicarbonate solution (60 ml)
  4. customAfter crystallization for 60 hours the solid
  5. customwas collected
  6. washwashed with ether and water

Sources & evidence

ORD record
ord-21f67a51acce4c379d0c1bf38c405b53
Source dataset
uspto-grants-2001_05
Patent number
US06228859B1

Reaction notes

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