Methanol → 2,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-methanol

HRID 1735135Notes

Reaction equation

HRID 1735135 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH2:17])[C:5]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([CH:15]=[O:16])[CH:9]=[N:8][C:6]=2[N:7]=1.CO.[BH4-].[Na+].O>CC(O)=O>[NH2:1][C:2]1[N:3]=[C:4]([NH2:17])[C:5]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([CH2:15][OH:16])[CH:9]=[N:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydride2×HCID 194368962,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-carboxaldehyde

Product 1

HCID 194368902,4-Diamino-5-propylpyrido[2,3-d]pyrimidine-6-methanolYield 83.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,4-Diamino-5-propylpyrido [2,3-d]pyrimidine-6-carboxaldehyde (95 mg, 0.41 mmol) was stirred with MeOH (20 mL), and the near-solution was treated with 3 portions of NaBH4 (17 mg total, 0.45 mmol) added at 15-min intervals. Complete solution occurred after the first addition of NaBH4. The solution was left at 20°-25° C. for 1 hour. The solution was treated with H2O (1 mL), neutralized to pH 7 with glacial AcOH, and evaporated to near dryness. Solid residue was stirred with a little cold H2O (~1 mL), collected, and dried to give a first crop of 6-hydroxymethyl compound (III-1, where R1 is propyl); yield 31% (30 mg). The filtrate from this compound was evaporated to dryness, and the residue was extracted several times with boiling EtOAc to provide additional product (80 mg).

Workup

  1. additionadded at 15-min intervals
  2. customevaporated
  3. customcollected
  4. customdried
  5. customto give a first crop of 6-hydroxymethyl compound (III-1, where R1 is propyl)
  6. customThe filtrate from this compound was evaporated to dryness
  7. extractionthe residue was extracted several times with boiling EtOAc

Sources & evidence

ORD record
ord-8261f02c226d4edc8b082bd8e3fb45d8
Source dataset
uspto-grants-1996_07
Patent number
US05536724

Reaction notes

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