Sodium Hydroxide → 2,4-Diamino-6-(hydroxymethyl)pyrido[2,3-d]pyrimidine

HRID 1248976

Reaction equation

HRID 1248976 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[C:5]([NH2:15])[C:6]2[CH:12]=[C:11]([CH:13]=[O:14])[CH:10]=[N:9][C:7]=2[N:8]=1.[OH-].[Na+].[BH4-].[Na+]>CC(N(C)C)=O>[NH2:2][C:3]1[N:4]=[C:5]([NH2:15])[C:6]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[N:9][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 129084762,4-Diaminopyrido[2,3-d]pyrimidine-6-carboxaldehyde hydrochloride

Product 1

HCID 4874162,4-Diamino-6-(hydroxymethyl)pyrido[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2,4-diaminopyrido[2,3-d]pyrimidine-6-carboxaldehyde hydrochloride (200 mg, 0.884 mmol) in DMAC (40 ml) at 0° C. was treated with 1N NaOH (0.884 ml, 0.884 mmol) followed by a suspension of NaBH4 (16.7 mg, 0.442 mmol) in DMAC (1 ml). The solution was stirred at 25° C. for 30 minutes and evaporated to dryness under high vacuum. A stirred suspension of the residue in H2O (5 ml) was adjusted to pH 3 with 6N HCl, stirred for 5 minutes and adjusted to pH 7 with 1N NaOH. The precipitate was collected by filtration, washed with H2O and dried in vacuo (P2O5); yield 121 mg (51%); mass spectrum, m/e 191 (M)+, 87 (M)+ for DMAC, 36 (M)+ for HCl; λmax nm (εx 10-3): 0.1N HCl-274 (6.91), 318 (8.21), 330 sh (7.17), 362 (1.77); pH 7-248 (18.1), 271 (9.85), 338 (6.52); 0.1N NaOH-248 (19.7), 271 (10.3), 345 (7.14).

Workup

  1. customevaporated to dryness under high vacuum
  2. additionA stirred suspension of the residue in H2O (5 ml)
  3. stirringstirred for 5 minutes
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with H2O
  6. dry with materialdried in vacuo (P2O5)

Sources & evidence

ORD record
ord-9228b1bc7a0b4358b53b8f339919365e
Source dataset
uspto-grants-1986_12
Patent number
US04628089

Linked notes

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