Dichloromethane → 6-Amino-3-methyl-5-(phenylmethylamino)pyrimidine-2,4-dione

HRID 275332Notes

Reaction equation

HRID 275332 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[N:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl.[BH3-]C#N.[Na+]>CC(O)=O.CO>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydride2×HCID 126359336-Amino-3-methyl-5-(phenylmethyleneamino)pyrimidine-2,4-dione

Product 1

HCID 125005046-Amino-3-methyl-5-(phenylmethylamino)pyrimidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

Add 6-amino-3-methyl-5-(phenylmethyleneamino )pyrimidine-2,4-dione (85 g=0.35 mol) to CH2Cl2 (1.6L) and MeOH (1.6L). Stir the suspension, add HOAc (21.9 ml=0.35 mol), then NaCNBH3 (21.9 g=0.35 mol). Stir 1.5 hr, and add HOAc (2 ml) and NaCNBH3 (2.0 g). After another 30 min, concentrate to ca. 1.6L on a rotovap (35° C. bath). Chill the crystalline mixture, filter, and wash with cold MeOH. Stir the product 15 min in 0.5L boiling MeOH, chill, filter, and dry to obtain the title compound, m.p. 206°-218° C.

Workup

  1. stirringStir 1.5 hr
  2. concentrationconcentrate to ca. 1.6L on a rotovap (35° C. bath)
  3. temperatureChill the crystalline mixture
  4. filtrationfilter
  5. washwash with cold MeOH
  6. stirringStir the product 15 min in 0.5L
  7. temperaturechill
  8. filtrationfilter
  9. customdry

Sources & evidence

ORD record
ord-15f14b0128334c6b9f13a48d723dfda9
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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