Cyclohexanemethanol → HCID 17941787, compound

HRID 1838965Notes

Reaction equation

HRID 1838965 reaction equation
[Na].[CH:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[NH2:10][C:11]1[N:16]=[C:15](Cl)[CH:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:12]=1>>[NH2:10][C:11]1[N:16]=[C:15]([O:9][CH2:8][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:14]=[C:13]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:12]=1

Participants

4

Reactant 3

HCID 7507CyclohexanemethanolHCID 14842704-N-benzyl-6-chloropyrimidine-2,4-diamineHCID 5360545Sodium

Product 1

HCID 17941787HCID 17941787, compoundYield 49%

Conditions

Temperature
180 °C

Procedure

To a stirred solution of sodium (0.025 g, 1.09 mmol) in cyclohexylmethanol (5 ml, 43 mmol) under nitrogen at 100° C., was added 2-amino-6-benzylamino-4-chloropyrimidine (0.2 g, 0.86 mmol), and the mixture was stirred at 180° C. for 2 h. After removal of solvents, the residue was redissolved in methanol, filtered and the filtrate was evaporated to dryness. The crude product was purified by chromatography on silica, employing petrol: ethyl acetate (8:2) as eluent, to give the title product as a yellow solid (0.13 g, 49%); δH (200 MHz, d6-DMSO) 0.96-1.15 (5H, m, C6H11), 1.23-1.34 (6H, m, C6H11), 4.03 (2H, br s, OCH2), 4.51 (2H, d, C6H5CH2, J=5.31 Hz), 5.12 (1H, s, C(5)H), 6.56 (2H, br s, NH2), 7.20 (1H, br s, NH), 7.28-7.39 (5H, m, C6H5); m/z (+EI) 312 (M+, 100%), 229 (M+-C6H11, 45), 216 (MH+-C6H11CH2, 53), 91 (72).

Workup

  1. customAfter removal of solvents
  2. dissolutionthe residue was redissolved in methanol
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. customThe crude product was purified by chromatography on silica

Sources & evidence

ORD record
ord-e69919f19d354e06860fc4951b80b2b0
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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