Sulfuric Acid → HCID 178497740, compound

HRID 2350866Notes

Reaction equation

HRID 2350866 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].NC(N)=N.[C:13]([CH:18]([C:33]#[N:34])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)(OCC)=[O:14].S(=O)(=O)(O)O>CN(C)C=O.CO>[NH2:4][C:3]1[N:5]=[C:33]([NH2:34])[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)=[C:13]([OH:14])[N:2]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 14796094HCID 14796094, compound

Product 1

HCID 178497740HCID 178497740, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.71 g (1.05 eq) of guanidine hydrochloride, 0.40 g (1.05 eq) of sodium methoxide, and 20 mL of anhydrous methanol is stirred under nitrogen for 30 minutes. The solid which forms is removed by filtration and the filtrate concentrated under reduced pressure. To the residue (guanidine free base) is added 2.15 g (1.0 eq) of methyl 4-(5-carbethoxy-5-cyanopentyl)benzoate in 20 mL of anhydrous dimethylformamide. This mixture is stirred under nitrogen with gentle heating for 12 hours, cooled, and then mixed with very dilute sulfuric acid. The solid is collected, washed with water and then diethyl ether, and dried to yield methyl 4-[4-(2,4-diamino-6-hydroxypyrimidin-5-yl)butyl]-benzoate, m.p. 203°-205° C.; IR (KBR) vmax 3495, 3380, 2925, 2850, 1685, 1600, 1490, 1430, 1359, 1282, 1174, 1111, 1015, and 754 cm-1 ; 1H NMR (d6DMSO) delta 9.74 (bs, 1H (3)--NH), 7.83 (d, J=8.1 Hz, 2H, Ar), 7.31 (d, J=8.1 Hz, 2H, Ar), 5.87 (bs, 2H (2)--NH2), 5.60 (bs, 2H, (6)--NH2), 3.80 (s, 3H, CH3), 2.62 (t, J=7.6 Hz, 2H, (5)--CH2), 2.15 (t, J=7.2 Hz, 2H, benzyl), 1.51-1.55 (m, 2H, 2° aliphatic), 1.26-1.28 (m, 2H 2° aliphatic).

Workup

  1. customThe solid which forms is removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. stirringThis mixture is stirred under nitrogen
  4. temperaturewith gentle heating for 12 hours
  5. temperaturecooled
  6. customThe solid is collected
  7. washwashed with water
  8. dry with materialdiethyl ether, and dried

Sources & evidence

ORD record
ord-122db312600f4fe49505d25241da49a6
Source dataset
uspto-grants-1989_10
Patent number
US04871743

Reaction notes

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