Methanol → Benzenemethanol, 4-((2,4-diamino-5-pyrimidinyl)methyl)-2,6-dimethoxy-

HRID 1579312Notes

Reaction equation

HRID 1579312 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.CO[C:13]([C:15]1[CH:20]=[C:19](OC)[C:18]([CH2:23][C:24]2[C:25]([NH2:31])=[N:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[C:17](OC)[CH:16]=1)=[O:14].[CH3:34][OH:35].O.[O:37]1CCOC[CH2:38]1>>[NH2:30][C:27]1[N:26]=[C:25]([NH2:31])[C:24]([CH2:23][C:18]2[CH:17]=[C:16]([O:37][CH3:38])[C:15]([CH2:13][OH:14])=[C:20]([O:35][CH3:34])[CH:19]=2)=[CH:29][N:28]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 312751,4-Dioxane3×HCID 21225700DiisobutylaluminumhydrideHCID 86732867HCID 86732867, compound

Product 1

HCID 108751Benzenemethanol, 4-((2,4-diamino-5-pyrimidinyl)methyl)-2,6-dimethoxy-

Conditions

Temperature
30 °C

Procedure

135 Ml. of about 15% diisobutylaluminum hydride solution in dioxane were added dropwise within 30 minutes at 50°C. under nitrogen and exclusion of moisture to a solution of 4.45 g. of α-(2,4-diamino-5-pyrimidinyl)-2,6-dimethoxy-p-toluic acid methyl ester in 400 ml. of absolute dioxane. The resulting suspension was stirred at 50° for 1 hour. After cooling to 30°C., the reaction mixture was treated with a mixture of 25 ml. of methanol, 5 ml. of water and 50 ml. of dioxane and stirred at 50° for an additional 2 hours. The solid material was separated and rejected, and the filtrate was evaporated to dryness. After recrystallization from about 20 ml. of methanol, the residue yielded 4-[ (2,4-diamino-5-pyrimidinyl)-methyl] -2,6-dimethoxybenzyl alcohol having a m.p. of 227°-228°.

Workup

  1. additionthe reaction mixture was treated with a mixture of 25 ml
  2. customThe solid material was separated
  3. customthe filtrate was evaporated to dryness
  4. customAfter recrystallization from about 20 ml

Sources & evidence

ORD record
ord-579ab1e390c8466c8639f156c3848aef
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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