Isopropanol → (4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)methanol

HRID 1617246Notes

Reaction equation

HRID 1617246 reaction equation
CC(C[AlH]CC(C)C)C.[NH2:10][C:11]1[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[CH:25][C:24]=2[O:33][CH3:34])=[C:13]([CH3:35])[N:12]=1.C(O)(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[NH2:10][C:11]1[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([CH2:27][OH:28])=[CH:25][C:24]=2[O:33][CH3:34])=[C:13]([CH3:35])[N:12]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14487Diisobutylaluminum hydrideHCID 24436Sodium SulfateHCID 68413361Methyl 4-((2-amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzoate

Product 1

HCID 68415232(4-((2-Amino-4-(butylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of DIBAL-H (80 ml, 1M in hexanes) was added portion wise over 20 min to a stirred solution of the product from step (ii) (3.8 g) in THF (25 mL) at 0° C. The mixture was allowed to warm to rt, stirred for 2 h, then cooled to 0° C. Isopropanol (2 mL) was added, stirred for 10 min and then added to a saturated solution of sodium sulfate (50 mL). The mixture was diluted with DCM (100 mL) and then stirred for 1 h. The organic phase was separated and the aqueous was extracted with DCM. The combined organic extracts were dried and filtered. The crude product was purified via silica chromatography (10% MeOHIDCM) to give the subtitle compound as a cream solid, 2.2 g.

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred for 10 min
  3. stirringstirred for 1 h
  4. customThe organic phase was separated
  5. extractionthe aqueous was extracted with DCM
  6. customThe combined organic extracts were dried
  7. filtrationfiltered
  8. customThe crude product was purified via silica chromatography (10% MeOHIDCM)

Sources & evidence

ORD record
ord-06a1537744d54679bfe14170feadbc4b
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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